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Journal articles on the topic 'Organic azide'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 April 2022

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1

Vikulina, E. L., E. E. Romashin, D. I. Fedorov, I. K. Kukushkin, A. M. Pyzhov, and P. P. Purygin. "METHOD OF REGENERATION OF AZIDE ION." Vestnik of Samara University. Natural Science Series 20, no. 7 (2017): 163–67. http://dx.doi.org/10.18287/2541-7525-2014-20-7-163-167.

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In this article the results of research devoted to the development of methods of disposal and regeneration of azide ion contained in the liquid wastes are stated. As a rule, all existing methods of disposal of azide ion in the liquid wastes based on its destruction, which is not only economically impractical because it is irretrievably lost, but also dangerous, as this forms an extremely explosive and toxic hydrazoic acid, which signiﬁcantly increases the risk of the process of disposal of liquid wastes. Researches carried out by the authors allowed for the ﬁrst time to suggest an eﬀective met

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2

Tchertanov, Luba. "Structural metrics relationships in covalently bonded organic azides." Acta Crystallographica Section B Structural Science 55, no. 5 (1999): 807–9. http://dx.doi.org/10.1107/s0108768199003936.

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Geometrical parameters of covalently bonded organic azides have been analysed using X-ray structural data retrieved from the Cambridge Structural Database. The RNNN fragment geometry shows some important general features: (i) a preference for a trans C s configuration; (ii) bending of the N—N—N unit; (iii) substantially different N—N bond lengths in the azide group. Electron-density redistribution within the covalently bonded azide group (relative to that in the isolated azide anion) promotes the capacity of the terminal azide N atom to form hydrogen bonds.

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3

Monticelli, Serena, and Vittorio Pace. "Diethylaluminium Azide: A Versatile Reagent in Organic Synthesis." Australian Journal of Chemistry 68, no. 5 (2015): 703. http://dx.doi.org/10.1071/ch14712.

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The unique properties of diethylaluminium azide – arising from the Lewis acid aluminium and the nucleophilicity of the azide – make it a versatile reagent in organic synthesis. Ring-opening of epoxides, Michael-type additions, synthesis of acyl azides, and functionalizations of fullerene C60 will be discussed. Among the recently described uses of the reagent, particular attention will be devoted to the powerful Sedelmeier’s method to access 1H-tetrazol starting from nitriles.

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4

Schock, Marvin, and Stefan Bräse. "Reactive & Efficient: Organic Azides as Cross-Linkers in Material Sciences." Molecules 25, no. 4 (2020): 1009. http://dx.doi.org/10.3390/molecules25041009.

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The exceptional reactivity of the azide group makes organic azides a highly versatile family of compounds in chemistry and the material sciences. One of the most prominent reactions employing organic azides is the regioselective copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition with alkynes yielding 1,2,3-triazoles. Other named reactions include the Staudinger reduction, the aza-Wittig reaction, and the Curtius rearrangement. The popularity of organic azides in material sciences is mostly based on their propensity to release nitrogen by thermal activation or photolysis. On the one hand, th

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5

Israr, Muhammad, Changqing Ye, Munira Taj Muhammad, Yajun Li, and Hongli Bao. "Copper(I)-catalyzed tandem reaction: synthesis of 1,4-disubstituted 1,2,3-triazoles from alkyl diacyl peroxides, azidotrimethylsilane, and alkynes." Beilstein Journal of Organic Chemistry 14 (November 23, 2018): 2916–22. http://dx.doi.org/10.3762/bjoc.14.270.

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A copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction for the synthesis of 1,4-disubstituted 1,2,3-triazoles from alkyl diacyl peroxides, azidotrimethylsilane, and terminal alkynes is reported. The alkyl carboxylic acids is for the first time being used as the alkyl azide precursors in the form of alkyl diacyl peroxides. This method avoids the necessity to handle organic azides, as they are generated in situ, making this protocol operationally simple. The Cu(I) catalyst not only participates in the alkyl diacyl peroxides decomposition to afford alkyl azides but also catalyzes the subs

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6

Roux, Amélie, and Federico Cisnetti. "Click Variations on the Synthesis of 2-Nitrophenyl-4-aryl-1,2,3-triazoles without Isolation of 2-Nitrophenyl Azides." Synlett 31, no. 06 (2019): 610–14. http://dx.doi.org/10.1055/s-0039-1691524.

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We report a series of efficient procedures to prepare 2-nitrophenyl-4-aryl-1,2,3-triazoles avoiding the isolation of potentially hazardous 2-nitrophenyl azides. An organocatalyzed azide-enolate variant allows efficient access to the target compounds while it was shown that a metal-catalyzed azide-alkyne procedure involving a preliminary Sonogashira coupling was feasible starting from electron-deficient aryl iodides.

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7

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 (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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8

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 (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,

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9

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 Me<sub>3</sub>SiN<sub>3</sub>.

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10

Adronov, Alex, Kelvin Li, and Stuart McNelles. "Preparation and Properties of a Hydrolytically Stable Cyclooctyne-Containing Polymer." Synlett 29, no. 19 (2018): 2535–41. http://dx.doi.org/10.1055/s-0037-1610636.

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A poly[(phenylene vinylene)-co-dibenzocyclooctyne] polymer prepared by Wittig polymerization chemistry between dibenzocyclooctyne bisaldehyde [DIBO-(CHO)2] and bis(triethyleneglycol)phenylbis(tributylphosphonium) dibromide is reported. The resulting polymer exhibits moderate molecular weight (Mn: 10.5 kDa, Mw: 21.3 kDa, Ð: 2.02) and is fluorescent. It could be readily functionalized by strain-promoted alkyne-azide cycloadditon with different azides, and fluorescence of the polymer was preserved after functionalization. Grafting azide-terminated 5 kDa poly(ethylene glycol) monomethyl ether chai

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11

Amyes, Tina L., Tadeusz Mizerski, and John P. Richard. "How does organic structure determine organic reactivity? The effect of ortho-dimethyl groups on the nucleophilic substitution and alkene-forming elimination reactions of ring-substituted cumyl derivatives." Canadian Journal of Chemistry 77, no. 5-6 (1999): 922–33. http://dx.doi.org/10.1139/v99-084.

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The addition of a pair of ortho-methyl groups to ring-substituted cumyl derivatives to give the corresponding 2,6-dimethylcumyl derivatives X-1-Y leads to modest (<5-fold) changes in the observed rate constant for reaction in 50:50 (v:v) trifluoroethanol-water (I = 0.50, NaClO4). The reactions of X-1-Y proceed by a stepwise mechanism through the liberated 2,6-dimethylcumyl carbocations X-2 that partition between nucleophilic addition of solvent and deprotonation to give good yields ([Formula: see text] 67%) of the corresponding 2-(2,6-dimethylaryl)propenes X-3. The carbocations X-2 are also

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12

Mata, Alejandro, Ulrich Weigl, Oliver Flögel, Pius Baur, Christopher A. Hone, and C. Oliver Kappe. "Acyl azide generation and amide bond formation in continuous-flow for the synthesis of peptides." Reaction Chemistry & Engineering 5, no. 4 (2020): 645–50. http://dx.doi.org/10.1039/d0re00034e.

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Acyl azides were safely generated by using nitrous acid in water and reacted in situ within a flow system. The acyl azide was efficiently extracted into the organic phase containing an amine nucleophile for a highly enantioselective peptide coupling.

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13

Chen, Fang-Fang, and Feng Wang. "Electronic Structure of the Azide Group in 3¢-Azido-3¢-deoxythymidine (AZT) Compared to Small Azide Compounds." Molecules 14, no. 7 (2009): 2656–68. http://dx.doi.org/10.3390/molecules14072656.

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14

Wu, Zhen, та Chen Zhu. "Synthesis of β-Difluoroalkyl Azides via 1,2-Azide Migration". Chinese Journal of Organic Chemistry 40, № 3 (2020): 808. http://dx.doi.org/10.6023/cjoc202000012.

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15

Kumasaki, Mieko, Kazushi Kinbara, Yuji Wada, Mitsuru Arai, and Masamitsu Tamura. "Azidoacetamide, a neutral small organic azide." Acta Crystallographica Section E Structure Reports Online 57, no. 1 (2000): o6—o8. http://dx.doi.org/10.1107/s160053680001850x.

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The structure of the title compound, C2H4N4O, was determined and found to be almost planar, excluding H atoms. The N—N bond lengths of 1.130 (2) and 1.231 (2) Å in the azide group exhibited a resonance effect and the characteristic organic azide structure.

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16

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 (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

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17

Zhou, Bingwei, Yunkui Liu, Hongwei Jin, and Daohong Liu. "One-Pot Copper-Catalyzed Three-Component Reaction of Sulfonyl Azides, Alkynes, and Allylamines To Access 2,3-Dihydro-1H-imidazo[1,2-a]indoles." Synthesis 52, no. 09 (2020): 1417–24. http://dx.doi.org/10.1055/s-0037-1610739.

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A copper-catalyzed multicomponent reaction of sulfonyl azides, alkynes, and allylamines affording 2,3-dihydro-1H-imidazo-[1,2-a]indoles in moderate yields is reported. Four C–N bonds are constructed by way of azide-alkyne cycloaddition (CuAAC) and double Ullmann-type coupling reactions in a one-pot process.

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18

Balci, Metin. "Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles." Synthesis 50, no. 07 (2018): 1373–401. http://dx.doi.org/10.1055/s-0036-1589527.

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Carbon–nitrogen bond formation is one of the most important reactions in organic chemistry. Various synthetic strategies for the generation of C–N bonds are described in the literature. For example, primary amines can be easily synthesized by the thermal decomposition of an acyl azide to an isocyanate, i.e. the Curtis rearrangement, followed by hydrolysis; the Curtius rearrangement has been used extensively. Furthermore, the advantage of the Curtius rearrangement is the isolation of acyl azides as well as the corresponding isocyanates. The isocyanates can be converted into various nitrogen-con

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19

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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20

Tripolszky, Anna, Krisztina Németh, Pál Tamás Szabó, and Erika Bálint. "Synthesis of (1,2,3-triazol-4-yl)methyl Phosphinates and (1,2,3-Triazol-4-yl)methyl Phosphates by Copper-Catalyzed Azide-Alkyne Cycloaddition." Molecules 24, no. 11 (2019): 2085. http://dx.doi.org/10.3390/molecules24112085.

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An efficient and practical method was developed for the synthesis of new (1,2,3‑triazol‑4‑yl)methyl phosphinates and (1,2,3-triazol-4-yl)methyl phosphates by the copper(I)‑catalyzed azide-alkyne cycloaddition (CuAAC) of organic azides and prop-2-ynyl phosphinate or prop-2-ynyl phosphate. The synthesis of (1‑benzyl-1H-1,2,3-triazol-4-yl)methyl diphenylphosphinate was optimized with respect to the reaction parameters, such as the temperature, reaction time, and catalyst loading. The approach was applied to a range of organic azides, which confirmed the wide scope and the substituent tolerance of

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21

Broxton, TJ, JR Christie, and RPT Chung. "Micellar Catalysis of Organic Reactions. XXVI. SNAr Reactions of Azide Ions." Australian Journal of Chemistry 42, no. 6 (1989): 855. http://dx.doi.org/10.1071/ch9890855.

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The azidodehalogenation of a number of aromatic compounds has been studied in the presence of micelles of cetyltrimethylammonium bromide (ctab). The variation of the observed rate of reaction with ctab concentration has been treated by using the model of Rodenas and Vera to determine the rate constant for reaction in the micellar pseudo-phase, k2m, the binding constant of the substrate to the micelle, Ks, and the nucleophile-micellar counter ion exchange constant KAzBr :. The ratio of the rate constants in the micellar pseudo-phase and in water varied between 0.9 and 52. For reactions involvin

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22

Kupracz, Lukas, Jan Hartwig, Jens Wegner, Sascha Ceylan, and Andreas Kirschning. "Multistep flow synthesis of vinyl azides and their use in the copper-catalyzed Huisgen-type cycloaddition under inductive-heating conditions." Beilstein Journal of Organic Chemistry 7 (October 20, 2011): 1441–48. http://dx.doi.org/10.3762/bjoc.7.168.

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The multistep flow synthesis of vinyl azides and their application in the synthesis of vinyltriazoles is reported. The synthesis relies on a stable polymer-bound equivalent of iodine azide that serves to carry out 1,2-functionalization of alkenes in a telescope flow protocol. The intermediate 2-iodo azides are subjected to a DBU-mediated polymer-supported elimination step yielding vinyl azides in good yield. The third step involves the formation of vinyl triazoles by a copper-catalyzed Huisgen-"click" cycloaddition. The required heat is generated by electromagnetic induction based on copper. C

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23

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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24

Bakherad, Mohammad, Ali Keivanloo, Amir H. Amin, and Amir Farkhondeh. "Synthesis of 1,2,3 triazole-linked benzimidazole through a copper-catalyzed click reaction." Heterocyclic Communications 25, no. 1 (2019): 122–29. http://dx.doi.org/10.1515/hc-2019-0016.

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AbstractAn efficient method has been developed for the synthesis of 1,2,3 triazole-linked benzimidazole through a copper-catalyzed click reaction in ethanol at 50°C. A broad range of aromatic azides were successfully reacted with n-propynylated benzimidazole via copper-catalyzed azide-alkyne cycloaddition reactions in the absence of a ligand. This method offers many advantages including short reaction times, low cost, and simple purification procedures.

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25

Wang, Gang-qiang, Li-li Yan, and Qiu-an Wang. "Synthesis and antiproliferative activity of flavonoid triazolyl glycosides." Heterocyclic Communications 24, no. 2 (2018): 119–24. http://dx.doi.org/10.1515/hc-2017-0241.

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AbstractSixteen flavonoid triazolyl glycosides4–19were synthesized in good yieldsviaCu(I)-catalyzed azide-alkyne cycloadditions of terminal alkynes of flavonoids1–3with acetylated sugar azides followed by deacetylation with sodium methoxide in anhydrous methanol. The antiproliferative activity of the synthesized compounds against three human cancer cell lines (Hela, HCC1954 and SK-OV-3)in vitrowas evaluated. Flavonoids1,2and flavonoid triazolyl glycosides7,12,17exhibit potent antiproliferative activity against these cancer cell lines.

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26

Warther, David, Enes Dursun, Marion Recher, et al. "Plasma induced acceleration and selectivity in strain-promoted azide–alkyne cycloadditions." Organic & Biomolecular Chemistry 19, no. 23 (2021): 5063–67. http://dx.doi.org/10.1039/d1ob00529d.

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We report the unexpected acceleration of strain-promoted azide–alkyne cycloaddition in human plasma compared to classical solvent systems. Besides fast kinetics, human plasma also allows for discrimination between two azides in competition reaction.

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27

Sultana, Jasmin, and Diganta Sarma. "Tetraamminecopper(II) Sulfate Monohydrate in Oxidative Azide-olefin Cyclo-addition and Three-component Click Reaction." Current Organic Synthesis 17, no. 1 (2020): 65–72. http://dx.doi.org/10.2174/1570179417666191223152643.

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Introduction: An effective Cu-complex, [Cu(NH3)4SO4 • H2O] was prepared conveniently from the inexpensive and easily available starting reagents in a simple route. Materials and Methods: Excellent reactivity of the catalyst was observed towards two competent clickcycloadditions: (a) oxidative cycloaddition of azides with electron-poor olefins and (b) one-pot cycloaddition of alkynes with boronic acid and sodium azide under “click-appropriate” conditions. Results: No external oxidant, short reaction time, high product yield, wide substrate scope, and aqueous solvent media make the azide-olefin

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28

Le, Giang Thanh, Giovanni Abbenante, Praveen K. Madala, Huy N. Hoang, and David P. Fairlie. "Organic Azide Inhibitors of Cysteine Proteases." Journal of the American Chemical Society 128, no. 38 (2006): 12396–97. http://dx.doi.org/10.1021/ja0637649.

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29

Fogel'zang, A. E., V. Yu Egorshev, V. P. Sinditskii, and M. D. Dutov. "Organic azide structure and combustion trends." Combustion, Explosion, and Shock Waves 26, no. 5 (1991): 558–64. http://dx.doi.org/10.1007/bf00843129.

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30

Zhu, Shizheng, Yong Xu, and Guifang Jin. "A novel synthesis of N-fluoroalkanesulfonylamidines using a three-component reaction." Canadian Journal of Chemistry 81, no. 4 (2003): 265–68. http://dx.doi.org/10.1139/v03-032.

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A novel, general, and efficient multicomponent reaction of fluoroalkanesulfonyl azides, secondary amines, and carbonyl compounds for the synthesis of N-fluoroalkanesulfonylamidines is presented. This reaction gave a good yield of products under very mild reaction conditions.Key words: multicomponent reactions, synthetic methods, N-fluoroalkanesulfonyl azide, N-fluoroalkanesulfonylamidine.

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31

Xiong, Jun, Qi-Xun Feng, Zhi-Ying Mu, et al. "Efficient Synthesis of 4H-3,1-Benzoxazine Derivatives via One-Pot Sequential Passerini-Azide/Palladium-Catalyzed Azide–Isocyanide Coupling/Cyclization Reaction." Synlett 31, no. 10 (2020): 1003–6. http://dx.doi.org/10.1055/s-0039-1690831.

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A new, one-pot method for the synthesis of 4H-3,1-benzoxazine derivatives has been developed. The Passerini-azide reactions of 2-azidobenzaldehydes, trimethylsilyl azide, and isocyanides produced azide intermediate without separation, which then reacted with isocyanides to give 4H-3,1-benzoxazine derivatives via a tandem one-pot palladium-catalyzed azide–isocyanide coupling/cyclization reaction in moderate to good yields.

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32

Vanhaecht, Stef, Jeroen Jacobs, Luc Van Meervelt, and Tatjana N. Parac-Vogt. "A versatile and highly efficient post-functionalization method for grafting organic molecules onto Anderson-type polyoxometalates." Dalton Transactions 44, no. 44 (2015): 19059–62. http://dx.doi.org/10.1039/c5dt03559g.

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33

Krespan, Carl G. "Fluoroalkyl azide chemistry." Journal of Organic Chemistry 51, no. 3 (1986): 332–37. http://dx.doi.org/10.1021/jo00353a011.

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34

Göbel, Dominik, Marius Friedrich, Enno Lork, and Boris J. Nachtsheim. "Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization." Beilstein Journal of Organic Chemistry 16 (July 14, 2020): 1683–92. http://dx.doi.org/10.3762/bjoc.16.139.

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Herein, we present a facile synthesis of three azide-functionalized fluorophores and their covalent attachment as triazoles in Huisgen-type cycloadditions with model alkynes. Besides two ortho- and para-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal alkynes, exhibiting different degrees of steric demand, was performed in high efficiency. Finally, we investigated the photophysical properties of the a

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35

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 (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-triphen

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36

Wei, Wen-Ting, Yan-Yun Liu, Wen-Hui Bao, et al. "Copper-Catalyzed C(sp3)–H Azidation of 1,3-Dihydro-2H-indol-2-ones Under Mild Conditions." Synlett 30, no. 01 (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-dihyd

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37

Wosińska-Hrydczuk, Marzena, Przemysław J. Boratyński та Jacek Skarżewski. "Regioselective and Stereodivergent Synthesis of Enantiomerically Pure Vic-Diamines from Chiral β-Amino Alcohols with 2-Pyridyl and 6-(2,2′-Bipyridyl) Moieties". Molecules 25, № 3 (2020): 727. http://dx.doi.org/10.3390/molecules25030727.

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In this report, we describe the synthetic elaboration of the easily available enantiomerically pure β-amino alcohols. Attempted direct substitution of the hydroxyl group by azido-functionality in the Mitsunobu reaction with hydrazoic acid was inefficient or led to a diastereomeric mixture. These outcomes resulted from the participation of aziridines. Intentionally performed internal Mitsunobu reaction of β-amino alcohols gave eight chiral aziridines in 45–82% yield. The structural and configuration identity of products was confirmed by NMR data compared to the DFT calculated GIAO values. For 1

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38

Czernecki, Stanislas, and Ebtissam Ayadi. "Preparation of diversely protected 2-azido-2-deoxyglycopyranoses from glycals." Canadian Journal of Chemistry 73, no. 3 (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–

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39

Lu, Yen-Chu, Shih-Chieh Kao, and Julian G. West. "Decatungstate-photocatalysed C(sp³)–H azidation." Chemical Communications 58, no. 31 (2022): 4869–72. http://dx.doi.org/10.1039/d2cc00425a.

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Tetrabutylammonium decatungstate (TBADT) functions as an efficient photocatalyst for the C(sp3) azidation of organic molecules using the commercial azide source para-acetamidobenzenesulfonyl azide (p-ABSA).

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40

Kapuściński, Szymon, Bindushree Anand, Paulina Bartos, Jose M. Garcia Fernandez, and Piotr Kaszyński. "Tethered Blatter Radical for Molecular Grafting: Synthesis of 6-Hydroxyhexyloxy, Hydroxymethyl, and Bis(hydroxymethyl) Derivatives and Their Functionalization." Molecules 27, no. 4 (2022): 1176. http://dx.doi.org/10.3390/molecules27041176.

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Synthetic access to 7-CF3-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl radicals containing 4-(6-hydroxyhexyloxy)phenyl, 4-hydroxymethylphenyl or 3,5-bis(hydroxymethyl)phenyl groups at the C(3) position and their conversion to tosylates and phosphates are described. The tosylates were used to obtain disulfides and an azide with good yields. The Blatter radical containing the azido group underwent a copper(I)-catalyzed azide–alkyne cycloaddition with phenylacetylene under mild conditions, giving the [1,2,3]triazole product in 84% yield. This indicates the suitability of the azido derivative for grafti

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Nishiyama, Kozaburo, and Tomoko Yamaguchi. "Selective Formation of Alkyl Azides Using Trimethylsilyl Azide and Carbonyl Compounds." Synthesis 1988, no. 02 (1988): 106–8. http://dx.doi.org/10.1055/s-1988-27481.

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Patonay, Tamás, József Jekö та Éva Rimán. "SYNTHESIS OF α-AZIDO-2′-HYDROXYCHALCONES FROM CHALCONE DIBROMIDES WITH AZIDE ION". Synthetic Communications 32, № 15 (2002): 2403–15. http://dx.doi.org/10.1081/scc-120006013.

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43

Xiong, Jun, Qing Min, Gang Yao, Jia-An Zhang, Hai-Feng Yu, and Ming-Wu Ding. "New Facile Synthesis of 3,4-Dihydroquinazoline-2(1H)-thiones by a Sequential Ugi-Azide/Staudinger/Aza-Wittig/Cyclization Reaction." Synlett 30, no. 09 (2019): 1053–56. http://dx.doi.org/10.1055/s-0037-1611817.

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A new facile synthesis of 3,4-dihydroquinazoline-2(1H)-thiones by an Ugi-azide/Staudinger/aza-Wittig/cyclization sequence has been developed. The Ugi-azide reactions of 2-azidobenzaldehydes, amines, trimethylsilyl azide, and isocyanides produced tetrazoles, which, when treated with methyldiphenylphosphane and CS2, produced 3,4-dihydroquinazoline-2(1H)-thiones in good overall yields via a sequential Staudinger/aza-Wittig/cyclization reaction.

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44

Arigela, Rajesh K., Sudhir K. Sharma, Brijesh Kumar, and Bijoy Kundu. "Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles." Beilstein Journal of Organic Chemistry 9 (February 19, 2013): 401–5. http://dx.doi.org/10.3762/bjoc.9.41.

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A microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide–internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the methodology has been demonstrated by treating various 2-alkynylindoles (aromatic/aliphatic) with epichlorohydrin and sodium azide furnishing annulated tetracyclic indolodiazepinotriazoles in satisfactory yields.

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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 (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 triazol

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Hamala, Vojtěch, Lucie Červenková Šťastná, Martin Kurfiřt, Petra Cuřínová, Martin Dračínský, and Jindřich Karban. "Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides." Beilstein Journal of Organic Chemistry 17 (May 11, 2021): 1086–95. http://dx.doi.org/10.3762/bjoc.17.85.

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Multiple fluorination of glycostructures has emerged as an attractive way of modulating their protein affinity, metabolic stability, and lipophilicity. Here we described the synthesis of a series of mono-, di- and trifluorinated N-acetyl-ᴅ-glucosamine and ᴅ-galactosamine analogs. The key intermediates are the corresponding multiply fluorinated glucosazide and galactosazide thioglycosides prepared from deoxyfluorinated 1,6-anhydro-2-azido-β-ᴅ-hexopyranose precursors by ring-opening reaction with phenyl trimethylsilyl sulfide. Nucleophilic deoxyfluorination at C4 and C6 by reaction with DAST, th

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Jiang, Yuqin, Kai Wu, Xuxia Tan, et al. "[bmim]PF6/KOH: A Recyclable Catalytic System for an Azide–Arylacetaldehyde [3 + 2] Cycloaddition." Journal of Chemical Research 41, no. 11 (2017): 631–35. http://dx.doi.org/10.3184/174751917x15094552081152.

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A fast and green protocol for the synthesis of 1,4-disubstituted 1,2,3-triazoles from azides and arylacetaldehydes at room temperature was developed using [bmim]PF6/KOH as the reaction medium. It was found that the in situ-generated carbene from [bmim]PF6/KOH acted as the catalyst. In the absence of a transition-metal catalyst and organic solvent, this azide–arylacetaldehyde [3 + 2] cycloaddition proceeds efficiently, with high levels of regioselectivity, broad range of substrates, excellent yields and simple operation under mild conditions.

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Araújo, Ana R. L., Augusto C. Tomé, Carla I. M. Santos, et al. "Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 2—Azides, Phthalocyanines, Subphthalocyanines and Porphyrazines." Molecules 25, no. 7 (2020): 1745. http://dx.doi.org/10.3390/molecules25071745.

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The reaction between organic azides and alkyne derivatives via the Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) is an efficient strategy to combine phthalocyanines and analogues with different materials. As examples of such materials, it can be considered the following ones: graphene oxide, carbon nanotubes, silica nanoparticles, gold nanoparticles, and quantum dots. This approach is also being relevant to conjugate phthalocyanines with carbohydrates and to obtain new sophisticated molecules; in such way, new systems with significant potential applications become available. This review h

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Leyva, Elisa, Matthew S. Platz, Silvia E. Loredo-Carrillo, and Johana Aguilar. "Fluoro Aryl Azides: Synthesis, Reactions and Applications." Current Organic Chemistry 24, no. 11 (2020): 1161–80. http://dx.doi.org/10.2174/1385272824999200608132505.

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Background: The complex photochemistry of aryl azides has fascinated scientists for several decades. Spectroscopists have investigated the intermediates formed by different analytical techniques. Theoretical chemists have explained the intrinsic interplay of intermediates under different experimental conditions. Objective & Method: A complete understanding of the photochemistry of a given fluoro aryl azide is a basic requisite for its use in chemistry. In this review, we will discuss the synthesis of several fluoro substituted aryl azides and the reactions and intermediates generated upon

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50

Wolfram, Stefanie, Hendryk Würfel, Stefanie H. Habenicht, et al. "A small azide-modified thiazole-based reporter molecule for fluorescence and mass spectrometric detection." Beilstein Journal of Organic Chemistry 10 (October 23, 2014): 2470–79. http://dx.doi.org/10.3762/bjoc.10.258.

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Molecular probes are widely used tools in chemical biology that allow tracing of bioactive metabolites and selective labeling of proteins and other biomacromolecules. A common structural motif for such probes consists of a reporter that can be attached by copper(I)-catalyzed 1,2,3-triazole formation between terminal alkynes and azides to a reactive headgroup. Here we introduce the synthesis and application of the new thiazole-based, azide-tagged reporter 4-(3-azidopropoxy)-5-(4-bromophenyl)-2-(pyridin-2-yl)thiazole for fluorescence, UV and mass spectrometry (MS) detection. This small fluoresce

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