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Journal articles on the topic 'Azidy'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Dong, Z., KA Hellmund, and SG Pyne. "Chiral Sulfur Compounds. XXI. Addition of Azide Ion to β-Aryl-α-phenylsulfinylacrylates." Australian Journal of Chemistry 46, no. 9 (1993): 1431. http://dx.doi.org/10.1071/ch9931431.

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The reaction of methyl β-aryl-α- phenylsulfinylacrylates (1) with sodium azide /acetic acid gives triazoles (6) while the reaction of (1) with sodium azide /hydrochloric acid gives β-azido esters (7a,b). Reaction of (7a) with 1,8-diazabicyclo[5.4.0]undec-7-ene, and (7b) with triethylamine gave the corresponding triazoles (6a) and (6b), respectively. Thus the formation of triazoles from the reaction of acrylates with azide ion most likely involves Michael addition of azide ion followed by cyclization of an incipient β-azido α-anion.

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2

Yang, Tonghao, Haizhen Zhu, and Wei Yu. "Copper-catalyzed radical reactions of 2-azido-N-arylacrylamides with 1-(trifluoromethyl)-1,2-benziodoxole and 1-azidyl-1,2-benziodoxole." Organic & Biomolecular Chemistry 14, no. 13 (2016): 3376–84. http://dx.doi.org/10.1039/c6ob00226a.

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The tandem addition/cyclization reactions of 2-azido-N-arylacrylamides with 1-(trifluoromethyl)-1,2-benziodoxole and 1-azidyl-1,2-benziodoxole-derived trifluoromethyl radicals and azidyl radicals were investigated.

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3

Zhao, Jiong-Peng, Cui Zhao, Wei-Chao Song, Lei Wang, Yabo Xie, Jian-Rong Li, and Xian-He Bu. "4-Substituent pyridine directed cobalt(ii) azides: solvothermal synthesis, structure, and magnetic properties." Dalton Transactions 44, no. 22 (2015): 10289–96. http://dx.doi.org/10.1039/c5dt00568j.

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Azido-bridged magnetic complexes: Different 4-substituent groups of pyridine co-ligands directed the linkages between azide and Co(ii) ions, to give three azide–Co(ii) complexes with different structures and magnetic properties.

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4

Forman, Grant S., Adrian Scaffidi, and Robert V. Stick. "An Alternative Synthesis of Some Carbohydrate α-Amino Acids." Australian Journal of Chemistry 57, no. 1 (2004): 25. http://dx.doi.org/10.1071/ch03214.

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Several carbohydrate ketones have been converted into their trichloromethyl-branched tertiary alcohols. A subsequent treatment of these alcohols under Corey–Link conditions (base, sodium azide, methanol) has given rise to α-azido esters, transformable into azido acids, amino esters, and amino acids. An amino ester and an azido acid have been coupled to form a dipeptide.

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5

Stamatatos, Theocharis C., and Eva Rentschler. "Organic chelate-free and azido-rich metal clusters and coordination polymers from the use of Me3SiN3: a new synthetic route to complexes with beautiful structures and diverse magnetic properties." Chemical Communications 55, no. 1 (2019): 11–26. http://dx.doi.org/10.1039/c8cc08854c.

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A new synthetic route to structurally novel and magnetically interesting 3d-metal azido clusters and coordination polymers is presented; the key reagent for the preparation of solely azido-bridged molecule-based species is the organic azide precursor Me₃SiN₃.

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6

Goher, Mohamed A. S., and Franz A. Mautner. "Preparation, Spectral and Structural Characterization of Two Polymeric 1:1 Mixed Ligand Complexes of Copper(II) Azide with 4-Methylquinoline and 2-Methylpyridine." Zeitschrift für Naturforschung B 46, no. 5 (May 1, 1991): 687–92. http://dx.doi.org/10.1515/znb-1991-0522.

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Two 1:1 mixed ligand complexes of copper(II) azide with substituted quinoline and pyridine, namely catena di-μ(1,1)-azido-(4-methylquinoline)copper(II) (1) and catena di-μ(1,3)-azido-[di-μ(1,1)-azido-bis(2-methylpyridine)dicopper(II)] (2) have been prepared and characterized by X-ray crystallography.Crystal data: 1, C10H9N7Cu, space group P21/c, a = 577.8(2), b = 2202.3(5), c = 919.9(2) pm, β = 93.92(2)°, Ζ = 4, and R = 0.035 for 1293 observed MoKa data; 2, C6H7N7Cu, space group P21/a, a = 823.7(2), b = 1303.8(4), c = 895.3(3) pm, β = 112.23(2)°, Ζ = 4, and R = 0.022 for 2133 observed ΜοΚα diffractometer data. In the structure of 1, the Cu(II) has a strongly distorted trigonal bypyramidal coordination, where both azido groups function as μ(1,1) bridging ligands resulting in a columnar structure along the a axis. The polymeric complex 2 has a less distorted square pyramidal structure; one half of the azide groups act as μ(1,1) bridging ligands to form centrosymmetric dimers. These dimeric units are further connected by the remaining μ(1,3) bridging azido groups to form layers within the ab-plane. Infrared and electronic spectral data are also presented and discussed.

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7

Resende, Diana I. S. P., Amalia M. Estévez, Andre M. Alker, Rainer E. Martin, and Hans Peter Wessel. "A carbohydrate-derived trifunctional scaffold for medicinal chemistry library synthesis." Mediterranean Journal of Chemistry 7, no. 2 (September 5, 2018): 135–44. http://dx.doi.org/10.13171/mjc72/01809051415-wessel.

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For the generation of compound libraries for drug discovery a central scaffold containing three exit vectors with defined chirality was devised starting from commercially available tri-O-acetyl-glucal. Surprisingly, the reaction of a 4-O-mesylate with sodium azide did not lead to the expected 4-azido-4-deoxy derivative but to a 3-azido-3-deoxy regioisomer via intermediate epoxide formation. The absolute stereochemical configuration of the final tetrahydropyran building block was proven by X-ray crystallography. This scaffold endowed with a carboxylic acid, a secondary alcohol, and an azide functionality may be connected to a DNA tag at any of the three distinct exit vectors, thus providing ready access to several different compound libraries.Â

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8

Kumar, Rakesh, Leonard I. Wiebe, and Edward E. Knaus. "A mild and efficient methodology for the synthesis of 5-halogeno uracil nucleosides that occurs via a 5-halogeno-6-azido-5,6-dihydro intermediate." Canadian Journal of Chemistry 72, no. 9 (September 1, 1994): 2005–10. http://dx.doi.org/10.1139/v94-256.

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A mild and efficient methodology for the synthesis of 5-halogeno (iodo, bromo, or chloro) uracil nucleosides has been developed. 5-Halo-2′-deoxyuridines 4a–c (84–95%), 5-halouridines 7a–c (45–95%), and 5-haloarabinouridines 8a–c (65–95%) were synthesized in good to excellent yields by the reaction of 2′-deoxyuridine (2), uridine (5), and arabinouridine (6), respectively, with iodine monochloride, or N-bromo (or chloro)succinimide, and sodium azide at 25–45 °C. These C-5 halogenation reactions proceed via a 5-halo-6-azido-5,6-dihydro intermediate (3), from which HN3 is eliminated, to yield the 5-halogeno uracil nucleoside. The 5-halo-6-azido-5,6-dihydro intermediate products (10a, 10b) could be isolated from the reaction of 3′,5′-di-O-acetyl-2′-deoxyuridine (9) with iodine monochloride or N-bromosuccinimide and sodium azide at 0 °C. The isolation of 10a, 10b indicates that the C-5 halogenation reaction proceeds via a 5-halo-6-azido-5,6-dihydro intermediate.

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9

Ge, Junying, Qiuping Ding, Man Yang, Tian He, and Yiyuan Peng. "Copper and manganese co-mediated cascade aza-Michael addition/cyclization and azidation of 1,3-enynes: regioselective synthesis of fully substituted azido pyrroles." Organic & Biomolecular Chemistry 18, no. 43 (2020): 8908–15. http://dx.doi.org/10.1039/d0ob01927e.

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10

Hema, Kuntrapakam, and Kana M. Sureshan. "Three-way competition in a topochemical reaction: permutative azide–alkyne cycloaddition reactions leading to a vast library of products in the crystal." CrystEngComm 20, no. 11 (2018): 1478–82. http://dx.doi.org/10.1039/c8ce00131f.

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11

Zhang, Xueying, Zhansong Zhang, Jin-Na Song, and Zikun Wang. "Reductive radical-initiated 1,2-C migration assisted by an azidyl group." Chemical Science 11, no. 30 (2020): 7921–26. http://dx.doi.org/10.1039/d0sc02559c.

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12

Laus, Gerhard, Mirco E. Kostner, Volker Kahlenberg, and Herwig Schottenberger. "Synthesis and reactions of 2-azido-1,3-di(benzyloxy)imidazolium hexafluoridophosphate." Zeitschrift für Naturforschung B 71, no. 9 (September 1, 2016): 997–1003. http://dx.doi.org/10.1515/znb-2016-0104.

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Abstract2-Azido-1,3-di(benzyloxy)imidazolium hexafluoridophosphate was obtained from the corresponding 2-bromo compound by reaction with sodium azide. Cycloaddition of the 2-azido compound with norbornene and norbornadiene gave the respective tricyclic aziridine and bicyclic azaoctadiene. Addition of triphenylphosphane yielded the phosphazide which upon heating eliminated dinitrogen to afford the phosphazene. The crystal structures of five compounds were determined by X-ray diffraction.

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13

Pathigoolla, Atchutarao, and Kana M. Sureshan. "The topochemical synthesis of triazole-linked homobasic DNA." Chemical Communications 52, no. 5 (2016): 886–88. http://dx.doi.org/10.1039/c5cc08834h.

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Triazolyl-DNA (^TLDNA), DNA wherein phosphodiester units are replaced by triazole units, is of great interest. By adopting Topochemical Azide–Alkyne Cycloaddition (TAAC) reaction, we have synthesized homobasic ^TLDNA oligomers. 5′-ethynyl-3′-azido-2′,3′,5′-tri-deoxycytosine, which crystallized with proximal placement of azide and alkyne units of adjacent molecules, underwent TAAC reaction to ^TLDNA oligomers.

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14

Pan, Xiuwei, Hao Gao, Guodong Fu, Yun Gao, and Weian Zhang. "Synthesis, characterization and chondrocyte culture of polyhedral oligomeric silsesquioxane (POSS)-containing hybrid hydrogels." RSC Advances 6, no. 28 (2016): 23471–78. http://dx.doi.org/10.1039/c5ra27989e.

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Polyhedral oligomeric silsesquioxanes (POSS)-based hybrid hydrogels were successfully prepared via a fast azide-alkyne click reaction between octa-azido-functionalized POSS (OAPOSS) and alkyne-functionalized poly(ethylene glycol) (PEG).

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15

Cherton, Jean-Claude, Paul-Louis Desbene, Marc Bazinet, Marc Lanson, Odile Convert, and Jean-Jacques Basselier. "Réactivité du nucléophile azoture vis à vis de cations hétérocycliques aromatiques. VI. Cas des triaryl-2,4,6 oxaziniums-1,3." Canadian Journal of Chemistry 63, no. 1 (January 1, 1985): 86–94. http://dx.doi.org/10.1139/v85-015.

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Nucleophilic attack of sodium azide on 2,4,6-triaryl-1,3-oxazinium species gives high yields of β-tetrazolo-trans-benzalacetophenones from the corresponding 2-azido-1,3-oxazines. The rearrangement of the azido oxazines likely proceeds via tautomerism of the intermediate iminoazides. If the formation of the 2-azido-1,3-oxazines is under kinetic control, these results are a rare example of high regioselectivity in nucleophilic attack at the C2 carbon of 1,3-oxazinium species.The reaction behaviour of the 1,3-oxazinium/N3− system is discussed, together with results obtained from the 2,4,6-triphenylpyrilium/N3−.

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16

Krist, Pavel, Marek Kuzma, István F. Pelyvás, Pavla Simerská, and Vladimír Křen. "Synthesis of 4-Nitrophenyl 2-Acetamido-2-deoxy-β-D-mannopyranoside and 4-Nitrophenyl 2-Acetamido-2-deoxy-α-D-mannopyranoside." Collection of Czechoslovak Chemical Communications 68, no. 4 (2003): 801–11. http://dx.doi.org/10.1135/cccc20030801.

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The title compounds were synthesized by the selective reduction of the azido group in 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside (8) and 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-mannopyranoside (11), and by subsequent acetylation. Compound 8 was prepared by opening of the epoxide ring in methyl 2,3-anhydro-4,6-O-benzylidene-α-D-glucopyranoside (1) with sodium azide, followed by inversion of the configuration at C-3 in the resulting altropyranoside and glycosidation with 4-nitrophenol.

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17

Su, Yaning, Li Li, Haibin Wang, Xiaochen Wang, and Zhiyuan Zhang. "All-in-One azides: empowered click reaction for in vivo labeling and imaging of biomolecules." Chemical Communications 52, no. 10 (2016): 2185–88. http://dx.doi.org/10.1039/c5cc08466k.

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We designed and synthesized All-in-One (AIO) reactive azide reagents for bioorthogonal reactions with highly efficient Cu(i) ligand moieties, an azido group, and functional tags for imaging or purification.

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18

Hu, Qiong, Xianbao Deng, Jinming Kong, Yuanyuan Dong, Qianrui Liu, and Xueji Zhang. "Simple and fast electrochemical detection of sequence-specific DNA via click chemistry-mediated labeling of hairpin DNA probes with ethynylferrocene." Analyst 140, no. 12 (2015): 4154–61. http://dx.doi.org/10.1039/c5an00566c.

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In this work, the azido-containing hairpins were exploited as the capture probes; after hybridization, labeling of electroactive probes, ethynylferrocene, was conveniently and efficiently achieved via the Cu(i)-catalyzed azide–alkyne cycloaddition.

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19

Czernecki, Stanislas, and Ebtissam Ayadi. "Preparation of diversely protected 2-azido-2-deoxyglycopyranoses from glycals." Canadian Journal of Chemistry 73, no. 3 (March 1, 1995): 343–50. http://dx.doi.org/10.1139/v95-046.

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A new and efficient preparation of diversely protected 2-azido-2-deoxyglycopyranosides from the corresponding glycals is described. The glycals are first transformed into protected phenyl 2-azido-2-deoxy-selenoglycopyranosides by azido-phenylselenylation. Two procedures were employed according to the protecting groups present: sodium azide and diphenyldiselenide in the presence of (diacetoxyiodo)benzene for peracetylated glycals (Procedure A) or trimethylsilyl azide and tetra-n-butylammonium fluoride in the presence of N-phenylselenophthalimide for perbenzylated glycals (Procedure B). A gluco–manno mixture (90%) is obtained from protected d-glucal whereas only the galacto isomer is formed from protected d-galactal (75%). The compatibility of the second procedure with one free hydroxyl group and a variety of protecting groups was verified with 1,5-anhydro-2-deoxy-3,4-O-isopropylidene-d-lyxo-hex-1-enitol and its 6-O-acetyl, 6-O-allyl, 6-O-benzyl, and 6-O-tert-butyldimethylsilyl derivatives as well as with 1,5-anhydro-4,6-O-benzylidene-2-deoxy-d-lyxo-hex-1-enitol and its 3-O-acetyl and 3-O-benzyl derivatives, which were transformed into phenyl 2-azido-2-deoxy-α-d-selenogalactopyranoside derivatives in good yield. In the second step, hydrolysis of these selenoglycosides afforded diversely protected glycopyranoses in high yield. Peracetylated derivatives were hydrolyzed in the presence of N-iodosuccinimide, whereas mercury trifluoroacetate was employed for 3,4-O-isopropylidene, 4,6-O-benzylidene, and perbenzylated derivatives. In some cases the two steps can be carried out without isolation of the intermediate selenoglycoside. Keywords: glycals, 2-azido-2-deoxygalactopyranose, 2-azido-2-deoxyglucopyranose, selenoglycosides.

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20

Yao, Kezi, Arnau Bertran, Jacques Morgan, Samuel M. Hare, Nicholas H. Rees, Alan M. Kenwright, Katharina Edkins, Alice M. Bowen, and Nicola J. Farrer. "A novel Pt(iv) mono azido mono triazolato complex evolves azidyl radicals following irradiation with visible light." Dalton Transactions 48, no. 19 (2019): 6416–20. http://dx.doi.org/10.1039/c9dt01156k.

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A novel Pt^IV azido triazolato complex exists as an equilibrium between two species in d₃-MeCN and evolves azide radicals (but not hydroxide radicals) when irradiated with visible light.

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21

Nasseri, Mohammad Ali, Seyyedeh Ameneh Alavi, Boshra Mahmoudi, and Milad Kazemnejadi. "A Facile Approach to Catalyst-Free Cyanation and Azidation of Organic Compounds and a One-Pot Preparation of 5-Substituted 1H-Tetrazoles by Using a Dimethyl Sulfoxide–Nitric Acid Combination." Synlett 30, no. 20 (October 31, 2019): 2290–94. http://dx.doi.org/10.1055/s-0039-1690742.

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In this study, cyanations or azidations of imines were performed by using hydroxy(dimethyl)-λ4-sulfanecarbonitrile or azido(dimethyl)-λ4-sulfanol, respectively, prepared in situ by treatment of potassium cyanide or sodium azide with a dimethyl sulfoxide–nitric acid combination. Furthermore, a one-pot preparation of 5-substituted 1H-tetrazole derivatives was carried out by using this reagent combination in the presence of an aldehyde, hydroxylamine hydrochloride, and sodium azide under mild conditions.

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22

Chapyshev, S. V., and E. N. Ushakov. "Tandem deprotonation/azide–tetrazole tautomerization of 4,6-diazido-N-nitro-1,3,5-triazin-2-amine in dimethylsulfoxide solutions: a theoretical study." Physical Chemistry Chemical Physics 17, no. 26 (2015): 17296–300. http://dx.doi.org/10.1039/c5cp02096d.

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4,6-Diazido-N-nitro-1,3,5-triazin-2-amine in DMSO-d₆ undergoes tandem deprotonation/azide–tetrazole tautomerization to yield the anionic form of 5-azido-N-nitrotetrazolo[1,5-a][1,3,5]triazin-7-amine.

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23

Yang, Xiaoming, Xinyu Lin, Li Yang, and Tonglai Zhang. "A novel method to synthesize stable nitrogen-rich polynitrobenzenes with π-stacking for high-energy-density energetic materials." Chemical Communications 54, no. 73 (2018): 10296–99. http://dx.doi.org/10.1039/c8cc05413d.

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A larger multi-nitro, multi-azide and multi-oxidized furazan ring compound with π–π stacking is herein reported. The coupling reaction of a NN bond and an azido was an efficient method to synthesize benzotriazole.

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24

Biewend, Michel, Philipp Michael, and Wolfgang H. Binder. "Detection of stress in polymers: mechanochemical activation of CuAAC click reactions in poly(urethane) networks." Soft Matter 16, no. 5 (2020): 1137–41. http://dx.doi.org/10.1039/c9sm02185j.

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We report on copper(i)-bis(N-heterocyclic carbene)s (NHC) for quantitative stress-sensing. This mechanophore is embedded within a polyurethane network, triggering a fluorogenic copper(i) azide alkyne cycloaddition (CuAAC) of 8-azido-2-naphtol and 3-hydroxy phenylacetylene.

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25

Velasco-Torrijos, Trinidad, and Róisín O’Flaherty. "Glycosylated α-Azido Amino Acids: Versatile Intermediates in the Synthesis of Neoglycoconjugates." Synlett 29, no. 07 (February 6, 2018): 904–7. http://dx.doi.org/10.1055/s-0036-1591902.

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A series of glycosylated α-azido amino acids was synthesized as precursors for neoglycoconjugates, a class of important biomolecules for drug discovery, and sensor development. The synthetically challenging 1,2-cis α-galactosylated species described herein were designed as building blocks in the synthesis of analogues of α-galactosyl ceramide, a potent immunomodulator. A benzyl-protected 1,2,3-triazolyl α-galactosyl-l-serine derivative was prepared using copper azide alkyne cycloaddition to showcase the potential of glycosylated α-azido amino acids in neoglycoconjugate design.

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26

Leclair, Alexandre, Rubén O. Torres-Ochoa, Qian Wang, and Jieping Zhu. "Iron-Catalysed Remote C(sp3)-H Azidation of O-Acyl Oximes and N -Acyloxy Imidates." CHIMIA International Journal for Chemistry 75, no. 4 (April 28, 2021): 329–32. http://dx.doi.org/10.2533/chimia.2021.329.

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The azido group occupies an important position in modern organic chemistry, broadly used as amine surrogates and as anchors in bioconjugation. Despite their importance, examples of selective direct azidation of inert C(sp3)–H bonds remain limited and often require strong oxidative conditions. Herein, we highlight the use of O-acyl oximes and N-acyloxy imidates as directing groups for the selective iron-catalysed azidation of C(sp3)–H bond with trimethylsilyl azide, giving access to various γ-azido ketones and β-azido alcohols in moderate to excellent yields. The iron catalyst is assumed to play a dual role in these catalytic processes: as a reductant to generate the reactive iminyl and imidate radicals, respectively, and as a redox centre to mediate the azido transfer to the translocated carbon radical.

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27

Buys, IE, LD Field, AV George, TW Hambley, and GR Purches. "Synthesis and Reactions of Azido Complexes of Ruthenium." Australian Journal of Chemistry 48, no. 1 (1995): 27. http://dx.doi.org/10.1071/ch9950027.

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Sodium azide reacts with RuH2 ( dmpe )2 (1a) ( dmpe = 1,2-bis( dimethylphosphino )ethane) in methanol solution to form RuH (N3)( dmpe )2 (2a), and reacts with RuCl2( depe )2 (3b) ( depe = 1,2-bis( diethylphosphino )ethane) to form the bis ( azide ) complex Ru (N3)2( depe )2 (4b). The crystal structures of Ru ( Cl )2( depe )2 (3b) and Ru (N3)2( depe )2 (4b) have been determined and indicate that the chloro groups in (3b) and the azido groups in (4b) are trans across the metal centre.

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28

Xu, Wan, Bing Hong Luo, Cai Rong Li, Jing Yang, and Chang Ren Zhou. "Synthesis and Characterization of Cholesterol-(1,2,3-triazole)-PEG via Click Chemistry." Advanced Materials Research 647 (January 2013): 499–503. http://dx.doi.org/10.4028/www.scientific.net/amr.647.499.

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Firstly, toluenesulfonyl cholesterol was synthesized by the reaction of cholesterol and p-toluenesulfonyl chloride, and then reacted with sodium azide to obtain azido-cholesterol. Secondly, propargyl was introduced into the terminal groups of polyethylene glycol (PEG) by the reaction of PEG and bromine propargyl. Lastly, cholesterol-(1,2,3-triazole)-PEG oligomer was prepared by the reaction of the azido-cholesterol and propargyl-PEG via click chemistry using CuSO4.5H2O as a catalyst. The structures of the products were characterized by the FTIR and 1H NMR analysis.

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29

Zullo, Valerio, Anna Iuliano, and Antonella Petri. "An Efficient and Practical Chemoenzymatic Route to (3R,3aR,6R,6aR)-Hexahydrofuro[3,2-b]furan-6-amino-3-ol (6-Aminoisomannide) from Renewable Sources." SynOpen 05, no. 03 (June 21, 2021): 161–66. http://dx.doi.org/10.1055/a-1532-5825.

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AbstractThe synthesis of 6-aminoisomannide is easily achieved starting from the renewable, inexpensive, and commercially available isosorbide in 66% overall yield. A biocatalyzed highly regioselective acetylation of the 3-endo hydroxyl group of isosorbide was followed by the stereospecific interconversion of the 6-exo hydroxyl group into an azido group, through reaction with trifluoromethanesulfonic anhydride, followed by nucleophilic displacement of the triflate group by sodium azide. Finally, reduction of the azido group and deacetylation of the 3-hydroxy group were performed in one pot using LiAlH4.

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30

Bock, Hans, and Ralph Dammel. "Gasphasen-Reaktionen, 58 [1, 2] β-Chlorethylazid: HCl-Eliminierung und Pyrolyse / Gas Phase Reactions, 58 [1, 2] β-Chloroethyl Azide: HCl Elimination and Pyrolysis." Zeitschrift für Naturforschung B 42, no. 3 (March 1, 1987): 301–7. http://dx.doi.org/10.1515/znb-1987-0309.

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The HCl elimination from β-chloroethyl azide (1-azido-2-chloroethane) over potassium tert. butanolate at 350 K in a low pressure flow system is optimized using PE spectroscopic real-time gas analysis. The highly explosive vinyl azide formed can be purified by cool-trapping the by-products. Its subsequent and virtually hazard-free pyrolysis yields 2H-azirine, which can be isolated at temperatures below 240 K.In contrast, the direct pyrolysis of β-chloroethyl azide requires temperatures above 710 K and results in a simultaneous split-off of both HCl and N2, yielding acetonitrile as the main thermolysis product. No intermediates such as β-chloroethanimine or ketenimine are observed, a result which is interpreted in terms of chemical activation

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31

Fajriyah, Nurul, Karno Karno, and Florentina Kusmiyati. "Induksi mutasi kedelai (Glycine max (L.) Merrill) dengan sodium azida pada tanah salin." Journal of Agro Complex 3, no. 1 (June 18, 2019): 1. http://dx.doi.org/10.14710/joac.3.1.1-8.

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ABSTRACT Mutation is one of plant breeding ways to expand genetic diversity. The purpose of the research was to evaluate the effect of sodium azide mutagen on soybean variety Dering 1 at saline and non-saline soil. The research was arranged in Factorial Design based on Completely Randomized Design with 2 factors. The first factor was doses of Sodium Azide consisted of 0 mM, 0.05 mM, 0.1 mM, 0.2 mM, dan 0.4 mM, 0.8 mM, 1.6 mM, 3.2 mM, 6.4 mM, 12.8 mM, and 25.6 mM. The second factor was salinity levels consisted of 0 dS/m, 2 dS/m and 5 dS/m. Parameters measured were plant height, number of leaves, number of pods, weight of pod, number of seeds, and weight of seeds per plant on M1 generation. Result showed that lethal dosage (LD) 50 was obtained at 0,663 mM. Sodium azide mutagent caused diversity of plant height, number of leaves at saline and non-saline soil. There was 10 plants and 3 plants that was classified as tolerant and most tolerant at saline soil (2 dS/m) respectively. Keywords : soybean, sodium azide, saline soil ABSTRAK Mutasi adalah salah satu cara pemuliaan tanaman untuk memperluas kergaman genetik. Tujuan penelitian untuk mengevaluasi pengaruh mutagen sodium azida terhadap kedelai varietas Dering 1 pada tanah salin dan non-salin. Rancangan percobaan yang digunakan di greenhouse adalah Percobaan Faktorial dengan dasar Rancangan Acak Lengkap yang terdiri dari 2 faktor. Faktor pertama adalah dosis mutagen kimia Sodium Azide (SA) yang terdiri dari 11 taraf perlakuan yaitu 0 mM, 0,05 mM, 0,1 mM, 0,2 mM, dan 0,4 mM, 0,8 mM, 1,6 mM, 3,2 mM, 6,4 mM, 12,8 mM, 25,6 mM. Faktor kedua adalah tingkat salinitas yaitu 0 dS/m, 2 dS/m dan 5 dS/m. Parameter yang diamati adalah tinggi tanaman, jumlah daun, jumlah polong, berat polong, jumlah biji, dan berat biji per tanaman pada generasi M1. Hasil penlitian menunjukkan bahwa dosis letal median (LD50) diperoleh pada 0,663 mM. Mutagen sodium azida menyebabkan keragaman tinggi tanaman, jumlah daun pada tanah salin dan non-salin. Terdapat 10 tanaman dan 3 tanaman yang masing-masing tergolong tahan dan sangat tahan pada tanah salin (2 dS/m). Kata kunci : kedelai, sodium azida, tanah salin

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32

Alfassi, Zeev B., Anthony Harriman, Robert E. Huie, S. Mosseri, and P. Neta. "The redox potential of the azide/azidyl couple." Journal of Physical Chemistry 91, no. 8 (April 1987): 2120–22. http://dx.doi.org/10.1021/j100292a029.

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33

Taher, Thuraya A., Waleed K. Mahdi, and Falih H. Musa. "Synthesis and Characterization of some Metal Complexes with (3Z ,5Z, 8Z)-2-azido-8-[azido(3Z,5Z)-2-azido-2,6bis(azidocarbonyl)-8,9-dihydro-2H-1,7-dioxa-3,4,5triazonine-9-yl]methyl]-9-[(1-azido-1-hydroxy)methyl]-2H1,7-dioxa-3,4,5-triazonine – 2,6 – dica." Ibn AL- Haitham Journal For Pure and Applied Science 30, no. 3 (December 28, 2017): 77. http://dx.doi.org/10.30526/30.3.1604.

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The reaction of LAs-Cl8 : [ (2,2- (1-(3,4-bis(carboxylicdichloromethoxy)-5-oxo-2,5dihydrofuran-2-yl)ethane – 1,2-diyl)bis(2,2-dichloroacetic acid)]with sodium azide in ethanol with drops of distilled water has been investigated . The new product L-AZ :(3Z ,5Z,8Z)-2azido-8-[azido(3Z,5Z)-2-azido-2,6-bis(azidocarbonyl)-8,9-dihydro-2H-1,7-dioxa-3,4,5triazonine-9-yl]methyl]-9-[(1-azido-1-hydroxy)methyl]-2H-1,7-dioxa-3,4,5-triazonine – 2,6 – dicarbonylazide was isolated and characterized by elemental analysis (C.H.N) , 1H-NMR , Mass spectrum and Fourier transform infrared spectrophotometer (FT-IR) . The reaction of the L-AZ withM+n: [ ( VO(II) , Cr(III) ,Mn(II) , Co(II) , Ni(II) , Cu(II) , Zn(II) , Cd(II) and Hg(II)] has been investigated and was isolated and characterized by FT- IR , UV-Visible ,electrical conductivity, magnetic susceptibilities at 22 Co . Atomic absorption and molar ratio Spectroscopic evidence showed that the binding of metal ions were through the azide(μ1,1-N3) Triazonine(3,5 –N3) and carboxyl moieties , resulting in a six – coordinating metal ions (Cr(III),Mn(II),Co(II),Ni(II) and Cu(II) ) .The VO(II) , Zn(II) ,Cd(II), andHg(II) were coordinated through azido (μ-1,1-N3) , triazonine(3,5-N3) only forming square pyramidal for VO(II) and tetrahedral geometry for Zn(II) , Cd(II) ,and Hg(II)β, ́ for Ni(II) , Cr(III) complexes were calculated too . The molar ratio and metal estimation showed , the ratio of LAZ to metal ions was (10:1) ; (M/L) .

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34

Bhatt, Suchitra, and Sandip K. Nayak. "Anhydrous Titanium(III) chloride as a New Lewis-Acid Catalyst for Ring Opening of Epoxides with Aromatic Amines." Natural Product Communications 2, no. 2 (February 2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200217.

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Anhydrous titanium(III) chloride was found to be a simple and efficient Lewis acid catalyst for ring opening of epoxides at ambient temperature. The reaction proceeded smoothly with anilines as well as azide ion as nucleophiles to give the corresponding β-amino alcohols and β-azido alcohols in moderate to good yields.

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35

Kore, Nitin, and Pavel Pazdera. "New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click” Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5-amine." Current Organic Synthesis 15, no. 4 (June 12, 2018): 552–65. http://dx.doi.org/10.2174/1570179415666180110152642.

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Aim and Objective: The aim of our work is to demonstrate catalytic application of our previously reported simple Cu(I) ion supported on weakly acidic polyacrylate resin for Azide-Alkyne cycloaddition (CuAAC), Azide-Nitrile cycloaddition and in synthesis of 1-azido-4-methoxybenzene. Material and Method: To investigate the catalytic ability of title Cu(I) catalyst we performed the reaction of different aryl azide with a broader spectrum of different terminal alkyne and nitrile compounds. Results: The title supported Cu(I) catalyzes cycloaddition reactions of aryl azide with aliphatic, aromatic, and heterocyclic terminal alkynes and corresponding 1,4-disubstituted 1,2,3-triazoles were obtained almost in the quantitative yields. The cycloaddition reactions of aryl azide with nitriles consisting α-hydrogen on carbon attached to cyano group under catalytic action of the title supported Cu(I) ended up with the formation of 1,4- disubstituted 1,2,3-triazol-5-amines in quantitative yields. The title catalyst found to be active for nucleophilic substitution of aide group (-N3) to 4-Iodoanisole. Conclusion: It was found that both studied Azide-Alkyne cycloaddition and Azide-Nitrile cycloaddition syntheses are regioselective and quantitative in yield. The title catalyst used is economical, easily preparable, separable, and recyclable. Therefore, the studied syntheses may be regarded as environmentally clean and green processes.

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36

Dyall, LK, and JA Ferguson. "Pyrolysis of Aryl Azides. XI. Enhanced Neighboring Group Effects of Carbonyl in a Locked Conformation." Australian Journal of Chemistry 45, no. 12 (1992): 1991. http://dx.doi.org/10.1071/ch9921991.

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Rates of pyrolysis in nitrobenzene solution have been measured for 1-azido-9H-fluoren-9- one, 1-azido-9H-xanthen-9-one, 1-azidoacridin-9(10H)-one and 1-azidoanthracene-9,1O-dione; relative to azidobenzene at 120� these were respectively 5.68, 1750, 5090 and 18400. The lack of neighbouring group participation for the first azide is related to the large distance between carbonyl oxygen and the inner azido nitrogen atom, and the data argue against a published proposal that the transition state is stabilized by electrostatic attraction. In the remaining azides, the 'locked conformation' leads to much larger neighbouring group assistance than is observed for freely rotating ortho groups such as benzoyl (krel79). Only the last azide yields an isoxazole on pyrolysis , the second and third ones providing the first reported examples of neighbouring -group-assisted pyrolysis in which no cyclic product is obtained. These results are interpreted in terms of an electrocyclic mechanism in which the transition state is early and N---0 bond formation is less advanced than other changes in bonds. Much of the rate enhancement is attributed to an electron distribution which favours nitrogen loss. 1-Aminoanthracen-9(10H)-one, 1-amino-9H-fluoren-9-one and 1-amino-9H-xanthen-9-one do not yield the corresponding isoxazoles when oxidative cyclization is attempted.

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37

Veinot, Alex J., Amber D. Blair, and Jason D. Masuda. "Crystal structure of 2-azido-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine." Acta Crystallographica Section E Crystallographic Communications 73, no. 6 (May 31, 2017): 905–7. http://dx.doi.org/10.1107/s2056989017007642.

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The title compound, C26H38N5P, was synthesized by reacting 2-chloro-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine with sodium azide and a catalytic amount of lithium chloride in tetrahydrofuran. The title compound is the first structurally characterized 2-azido-1,3,2-diazaphospholidine and exhibits a P atom in a trigonal pyramidal geometry. The azide P—N bond length of 1.8547 (16) Å is significantly longer than the P—N separations for the chelating diamine [P—N = 1.6680 (15) and 1.6684 (14) Å]. The sterically hindered 2,6-diisopropylphenyl groups twist away from the central heterocycle, with dihedral angles between the central heteocyclic ring and benzene rings of 76.17 (10) and 79.74 (9)°. In the crystal, a weak C—H...N link to the terminal N atom of the azide group leads to [100] chains.

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38

Liang, Xiao-Qin, Jin-Jun Zhou, Yan Zheng, and Feng Ma. "Theoretical Studies on the Mechanism of the Azido-Tetrazole of Azido-s-triazine." Natural Product Communications 10, no. 2 (February 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000213.

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The B3LYP/aug-cc-pvDZ level of theory has been applied to the study of the molecular structures, electronic structures and the azido-tetrazole isomerization of 1-azido-s-triazine, 1,3-diazido-s-triazine and 1,3,5-triazido-s-triazine. NBO analysis was applied to investigate the atomic natural charge and stabilization interaction energies among molecules. The results showed that the reaction initially proceeds through the loss of the linearity of the azido group and the approaching of the terminal nitrogen atom of the azide group to the nitrogen atom of the ring. This is followed by an attack of the lone pairs on N atoms in the ring to the azido group, leading to the formation of the N-N bonds. Many factors, including bending of the bond angle, electrostatic attraction, orbital delocalization and the stabilization interaction give rise to a large free energy barrier for the cyclization process. The results also show that the second and third cyclization is relatively easier than the first one.

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39

Nakano, Shun, Akihito Hashidzume, and Takahiro Sato. "Quarternization of 3-azido-1-propyne oligomers obtained by copper(I)-catalyzed azide–alkyne cycloaddition polymerization." Beilstein Journal of Organic Chemistry 11 (June 18, 2015): 1037–42. http://dx.doi.org/10.3762/bjoc.11.116.

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3-Azido-1-propyne oligomer (oligoAP) samples, prepared by copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) polymerization, were quarternized quantitatively with methyl iodide in sulfolane at 60 °C to obtain soluble oligomers. The conformation of the quarternized oligoAP in dilute DMSO-d 6 solution was examined by pulse-field-gradient spin-echo NMR based on the touched bead model.

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40

Protiva, Jiří, Thi Thu Huong Nguyen, Jiří Urban, and Eva Klinotová. "Reactions of 21-Acetoxy-16α,17α-epoxypregn-4-ene-3,20-dione with Nitrogen-Containing Nucleophilic Agents." Collection of Czechoslovak Chemical Communications 62, no. 7 (1997): 1095–104. http://dx.doi.org/10.1135/cccc19971095.

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21-Acetoxy-16α,17α-epoxypregn-4-ene-3,20-dione (1) enters a reaction with acetonitrile catalyzed by perchloric acid, giving unusual products with the furostane skeleton. In contrast to analogous reactions, the reaction with sodium azide results in the azido derivative possessing the non-rearranged ring D. The 1H NMR, 13C NMR, and mass spectra are discussed.

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41

Wei, Wen-Ting, Yan-Yun Liu, Wen-Hui Bao, Le-Han Gao, Wei-Wei Ying, Wei-Ting Chen, Gan-Ping Chen, and Qiang Li. "Copper-Catalyzed C(sp3)–H Azidation of 1,3-Dihydro-2H-indol-2-ones Under Mild Conditions." Synlett 30, no. 01 (November 14, 2018): 109–13. http://dx.doi.org/10.1055/s-0037-1610672.

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A simple and economical synthesis of 3-substituted 3-azido-1,3-dihydro-2H-indol-2-ones has been realized under mild conditions through copper-catalyzed C(sp3)–H azidation of the corresponding 1,3-dihydro-2H-indol-2-ones with trimethylsilyl azide. The reaction proceeds by an efficient pathway involving the addition of a N3 radical to the enol tautomer and consecutive C(sp3)−N bond formations. The method is valuable because of its mild reaction conditions, short reaction times, and broad substrate scope, and because of the rich biological activity of the resulting 3-substituted 3-azido-1,3-dihydro-2H-indol-2-one products.

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42

Maldotti, Andrea, Rossano Amadelli, and Vittorio Carassiti. "An electron spin resonance spin trapping investigation of azide oxidation on TiO2 powder suspensions." Canadian Journal of Chemistry 66, no. 1 (January 1, 1988): 76–80. http://dx.doi.org/10.1139/v88-011.

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The oxidation of azide has been studied on TiO2 powder suspensions in water, methanol, and mixtures of the two solvents. The esr spin trapping technique has been employed to provide evidence for the formation of azidyl radicals [Formula: see text]. The results show that an aqueous alkaline medium is necessary to obtain a high production of [Formula: see text] radicals. A mechanism is proposed whereby the oxidation of [Formula: see text] is mainly due to reaction with OH• radicals which are in turn generated upon capture of holes by OH− groups adsorbed on TiO2. Azidyl anions adsorb weakly on TiO2 and do not displace adsorbed OH− from the surface.

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43

Mocerino, M., and RV Stick. "The Synthesis of (2S,3R)-2-Hydroxymethylpiperidin-3-ol, a Fragment of the Alkaloid Swainsonine." Australian Journal of Chemistry 43, no. 7 (1990): 1183. http://dx.doi.org/10.1071/ch9901183.

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Methyl α- and β-D-galactopyranoside have been converted into methyl 4,6-di-O-benzyl-2,3-dideoxy-α- and -β-D-threo-hexoside , and subsequent treatment with ethanedithiol gives the same alcohol. Tosylation and azide displacement gives, after hydrolysis, an azido aldehyde which is transformed under reducing conditions into the title piperidine . The synthetic piperidine is an ineffective inhibitor of α-D- mannosidase.

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44

Cheng, Ya-Qian, Mao-Lin Hu, Shun Wang, and Ming-De Ye. "μ1,3-Azido-diazidotetrakis(1,10-phenanthroline)dicopper(II) azide tetrahydrate." Acta Crystallographica Section C Crystal Structure Communications 58, no. 1 (December 14, 2001): m12—m13. http://dx.doi.org/10.1107/s0108270101016948.

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45

Edwards, O. E., J. L. Douglas, D. C. Horwell, W. Rank, and T. Sano. "Thermal and photochemical reactions of steroidal α-azido ketones." Canadian Journal of Chemistry 70, no. 9 (September 1, 1992): 2405–12. http://dx.doi.org/10.1139/v92-305.

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Photolysis of 9α-azido-3β,20β-diacetoxy-5α-pregnan-11-one in methanol gave the N-acyl imine 11-aza-3β,20β-diacetoxy-C-homo-5α-pregn-9,11-en-12-one 4 and the aminoketone 9a-aza-3β,20β-diacetoxy-9-methoxy-B-homo-5α-pregnan-11-one 7. In dichloromethane containing triethylamine the irradiation of this azide gave the N-acyl imine 4 and the α,β-unsaturated amino ketone 9a-aza-3β,20β-diacetoxy-B-homo-5α-pregn-8-en-11-one 8. Thermolysis or photolysis of 12α-azido-3α,20β-diacetoxy-5β-pregnan-11-one gave the N-acyl imine 12-aza-3α,20β-diacetoxy-C-homo-5β-pregn-12-en-11-one 10 as major product. Photolysis of 20β-acetoxy-12α-azido-3α-hydroxy-5β-pregnan-11-one gave the 3-hydroxy analogue of 10. Transformation products of the N-acyl imines are described.

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46

Ma, Jie, Deng-Feng Wang, Li-Qun Fan, and Kang Zhou. "Structure and magnetic properties of a copper(II) coordination polymer based on azide, pyridine and homophthalic acid." Acta Crystallographica Section C Structural Chemistry 71, no. 11 (October 13, 2015): 969–74. http://dx.doi.org/10.1107/s2053229615018173.

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The azide anion is a short bridging ligand that has been used extensively to construct magnetic coordination polymers, and fundamental magneto-structural correlations have been substantiated by theoretical calculations. The copper(II) coordination polymer poly[bis(μ-azido-κ2N1:N1)(μ4-homophthalato-κ4O:O′:O′′:O′′′)bis(pyridine-κN)dicopper(II)], [Cu2(C9H6O4)(N3)2(C5H5N)2]n, was synthesized from homophthalic acid (2-carboxyphenylacetic acid), pyridine and azide (N3−) by a hydrothermal reaction. Single-crystal structure analysis indicated that it features a one-dimensional chain structure which is comprised of (μ1,1-N3−)(μ-syn–syn-COO−)2- and (μ1,1-N3−)2-bridged tetranuclear CuIIunits. Magnetic measurements revealed that the compound exhibits dominant antiferromagnetic behaviour.

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47

Matassini, Camilla, Stefania Mirabella, Andrea Goti, Inmaculada Robina, Antonio J. Moreno-Vargas, and Francesca Cardona. "Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar." Beilstein Journal of Organic Chemistry 11 (December 16, 2015): 2631–40. http://dx.doi.org/10.3762/bjoc.11.282.

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The synthesis of new multivalent architectures based on a trihydroxypiperidine α-fucosidase inhibitor is reported herein. Tetravalent and nonavalent dendrimers were obtained by means of the click chemistry approach involving the copper azide-alkyne-catalyzed cycloaddition (CuAAC) between suitable scaffolds bearing terminal alkyne moieties and an azido-functionalized piperidine as the bioactive moiety. A preliminary biological investigation is also reported towards commercially available and human glycosidases.

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48

Tsyrenova, Biligma, and Valentine Nenajdenko. "Synthesis and Spectral Study of a New Family of 2,5-Diaryltriazoles Having Restricted Rotation of the 5-Aryl Substituent." Molecules 25, no. 3 (January 23, 2020): 480. http://dx.doi.org/10.3390/molecules25030480.

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Efficient synthesis of 2,5-diaryl substituted 4-azido-1,2,3-triazoles by the reaction of sodium azide with dichlorosubstituted diazadienes was demonstrated. The optical properties of the prepared azidotriazoles were studied to reveal a luminescence maximum in the 360–420 nm region. To improve the luminescence quantum yields a family of 4-azido-1,2,3-triazoles bearing ortho-propargyloxy substituents in the 5 position was prepared. Subsequent intramolecular thermal cyclization permits to construct additional triazole fragment and obtain unique benzoxazocine derivatives condensed with two triazole rings. This new family of condensed heterocycles has a flattened heterocyclic system structure to provide more conjugation of the 5-aryl fragment with the triazole core. As a result, a new type of UV/“blue light-emitting” materials with better photophysical properties was obtained.

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49

Scaffidi, Adrian, Brian W. Skelton, Robert V. Stick, and Allan H. White. "The Synthesis of Carbohydrate α-Amino Acids Utilizing the Corey - Link Reaction." Australian Journal of Chemistry 57, no. 8 (2004): 723. http://dx.doi.org/10.1071/ch04015.

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Various carbohydrate ketones (uloses) have been treated with chloroform under strongly basic conditions to yield trichloromethyl tertiary alcohols. These alcohols, when subjected to the conditions of the modified Corey–Link reaction (sodium azide and 1,8-diazabicyclo[5.4.0]undec-7-ene in methanol), generally gave the expected azido ester with complete stereocontrol. Subsequent transformations on these azido esters provided amino esters, azido acids, and, in one case, the amino acid. A similar sequence applied to a protected d-glucono-1,5-lactone was only partly successful. Single-crystal X-ray structures are reported for 1,2:5,6-di-O-isopropylidene-3-C-trichloromethyl-α-d-allose, (3S)-3-C-azido-3-C-carboxy-3-deoxy-1,2:5,6-di-O-isopropylidene-α-d-ribo-hexose, 1,2:5,6-di-O-cyclohexylidene-3-C-trichloromethyl-α-d-gulose, (3S)-3-C-amino-1,2:5,6-di-O-cyclohexylidene-3-deoxy-3-C-methoxycarbonyl-α-d-xylo-hexose, methyl 2-O-benzyl-4,6-O-benzylidene-3-C-trichloromethyl-α-d-alloside, methyl (2S)-2-C-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methoxycarbonyl-α-d-arabino-hexoside, methyl 2,3-di-O-benzyl-6-deoxy-4-C-trichloromethyl-β-d-galactoside, 3,4,5,7-tetra-O-benzyl-1,1,1-trichloro-1-deoxy-α-d-gluco-hept-2-ulose, and 5-O-benzyl-1,2-O-isopropylidene-3-C-trichloromethyl-α-d-ribose.

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50

Cruchter, Thomas, Klaus Harms, and Eric Meggers. "Strain‐Promoted Azide–Alkyne Cycloaddition with Ruthenium(II)–Azido Complexes." Chemistry – A European Journal 19, no. 49 (October 31, 2013): 16682–89. http://dx.doi.org/10.1002/chem.201302502.

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