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Journal articles on the topic 'Cyclic carbamate'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 February 2022

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1

McElroy, C. Robert, Fabio Aricò, Franco Benetollo, and Pietro Tundo. "Cyclization reaction of amines with dialkyl carbonates to yield 1,3-oxazinan-2-ones." Pure and Applied Chemistry 84, no. 3 (2011): 707–19. http://dx.doi.org/10.1351/pac-con-11-07-18.

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A number of six-membered cyclic carbamates (oxazinanones) were synthesized from the reaction of a primary amine or hydrazine with a dicarbonate derivative of 1,3-diols in a one-pot reaction, in good yield, short time span, and in the absence of a solvent. The reaction proceeds in two steps: an intermolecular reaction to give a linear intermediate and an intramolecular cyclization to yield the cyclic carbamate. This is the first example of a carbonate reacting selectively and sequentially, firstly at the carbonyl center to form a linear carbamate and then as a leaving group to yield a cyclic ca

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2

Sauerberg, Per, June Chen, Elizabeth WoldeMussie, and Henry Rapoport. "Cyclic carbamate analogs of pilocarpine." Journal of Medicinal Chemistry 32, no. 6 (1989): 1322–26. http://dx.doi.org/10.1021/jm00126a030.

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3

Mocilac, Pavle, and John F. Gallagher. "Two isostructural carbamates: theo-tolylN-(pyridin-3-yl)carbamate and 2-bromophenylN-(pyridin-3-yl)carbamate monohydrates." Acta Crystallographica Section E Crystallographic Communications 71, no. 11 (2015): 1366–70. http://dx.doi.org/10.1107/s2056989015019556.

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The title carbamate monohydrates, C13H12N2O2·H2O and C12H9BrN2O2·H2O, form isomorphous crystals that are isostructural in their primary hydrogen-bonding modes. In both carbamates, the primary hydrogen bonding and aggregation involves cyclic amide–water–pyridine moieties as (N—H...O—H...N)2dimers about inversion centres [asR44(14) rings], where the participation of strong hydrogen-bonding donors and acceptors is maximized. The remaining water–carbonyl O—H...O=C interaction extends the aggregation into two-dimensional planar sheets that stack parallel to the (100) plane. The Br derivative does n

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4

Sakaitani, Masahiro, and Yasufumi Ohfune. "Syntheses and reactions of silyl carbamates. 2. A new mode of cyclic carbamate formation from tert-butyldimethylsilyl carbamate." Journal of the American Chemical Society 112, no. 3 (1990): 1150–58. http://dx.doi.org/10.1021/ja00159a040.

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5

McAuliffe, Joseph C., Brian W. Skelton, Robert V. Stick та Allan H. White. "β-Acarbose. IV. Model Studies on the Alkylation of Cyclohexylamine with a Carbohydrate Epoxide". Australian Journal of Chemistry 50, № 3 (1997): 209. http://dx.doi.org/10.1071/c96154.

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1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactose has been treated with cyclohexylamine to give an amino alcohol, convertible into 2,3-di-O-acetyl-1,6-anhydro-4-cyclohexylamino-4-deoxy-β-D-glucose by reduction and acetylation. The anhydro bridge of this diacetate has been successfully opened under acetolysis conditions. The original amino alcohol has also been converted into a cyclic carbamate, a carbamate and an aziridine, by utilizing a variety of reagents and conditions. The 1,6-anhydro bridge of the cyclic carbamate, also containing a 2-O-benzyl ether, could be opened under acetolysis conditions

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6

Tilbrook, Matthew G., Robert V. Stick та Spencer J. Williams. "β-Acarbose. VII. Approaches Towards the Synthesis of Some N-Linked Carba-Oligosaccharides". Australian Journal of Chemistry 52, № 9 (1999): 885. http://dx.doi.org/10.1071/ch99030.

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3,4-Anhydro-1,6-dideoxy-1,6-episeleno-β-D-glucose was treated with cyclohexylamine to afford an amino diol which was subsequently converted into a cyclic carbamate, a compound shown to be a moderately successful glycosyl donor. Treatment of the same 3,4-anhydro sugar and the 1,6-epithio analogue with a 1-epivalienamine derivative afforded the corresponding secondary amines which were converted into the analogous cyclic carbamates. The epithio analogue was unsuccessful as a glycosyl donor, failing to glycosylate a carbohydrate alcohol. On the other hand, the episeleno compound appeared to funct

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7

McAuliffe, Joseph C., та Robert V. Stick. "β-Acarbose. V. The Synthesis of a Hydroxylated Derivative of a Diastereoisomer of Methyl Acarviosin". Australian Journal of Chemistry 50, № 3 (1997): 219. http://dx.doi.org/10.1071/c96155.

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The treatment of a 1-epivalienamine derivative with 1,6:3,4-dianhydro-2-O-benzyl-β-D-galactose has given an amino alcohol capable of conversion into either a cyclic carbamate or an aziridine. All attempts at acetolysis of the 1,6-anhydro ring of the cyclic carbamate failed owing to the inherent reactivity of the (allylic) benzyl ethers present in the molecule. Therefore, following a reduction with lithium in ammonia and acetylation of the product, a new cyclic carbamate was obtained which underwent successful acetolysis to provide a heptaacetate. This heptaacetate could be transformed into the

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8

Aeyad, Tahani, Jason Williams, Anthony Meijer, and Iain Coldham. "Lithiation–Substitution of N-Boc-2-phenylazepane." Synlett 28, no. 20 (2017): 2765–68. http://dx.doi.org/10.1055/s-0036-1590857.

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Preparation of 2,2-disubstituted azepanes was accomplished from N-tert-butoxy(N-Boc)-2-phenylazepane by treatment with butyllithium then electrophilic quench. The lithiation was followed by in situ ReactIR spectroscopy and the rate of rotation of the carbamate was determined by variable temperature (VT)-NMR spectroscopy and by DFT studies. Most electrophiles add α to the nitrogen atom but cyanoformates and chloroformates gave ortho-substituted products. Cyclic carbamates were formed from an aldehyde or ketone electrophile. Kinetic resolution with sparteine was only poorly selective. Removal of

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9

Bresciani, Giulio, Marco Bortoluzzi, Claudia Ghelarducci, Fabio Marchetti та Guido Pampaloni. "Synthesis of α-alkylidene cyclic carbonates via CO2 fixation under ambient conditions promoted by an easily available silver carbamate". New Journal of Chemistry 45, № 9 (2021): 4340–46. http://dx.doi.org/10.1039/d0nj05657j.

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10

Fletcher, M. H., C. E. Burns-Lynch, K. W. Knouse, L. T. Abraham, C. W. DeBrosse, and W. M. Wuest. "A novel application of the Staudinger ligation to access neutral cyclic di-nucleotide analog precursors via a divergent method." RSC Advances 7, no. 47 (2017): 29835–38. http://dx.doi.org/10.1039/c7ra06045a.

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Herein we present a scalable and divergent synthesis of cyclic di-nucleotide analog precursors facilitated by differentiated di-amino sugars and a Staudinger ligation to provide medium-sized macrocycles featuring carbamate or urea linkages.

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11

Mudithanapelli, Chandrashekar, and Mi-hyun Kim. "Metal-free late-stage C(sp2)–H functionalization of N-aryl amines with various sodium salts." Organic & Biomolecular Chemistry 18, no. 3 (2020): 450–64. http://dx.doi.org/10.1039/c9ob02217a.

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Metal-free consecutive C(sp<sup>2</sup>)–X (X = Cl, Br, S, N) bond formations of N-aryl amines (cyclic, fused, carbamate, and aminium radicals) were achieved under mild conditions using PIFA and simple nonharmful sodium salts.

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12

Jeschke, Steffen, Ann-Christin Gentschev, and Hans-Dieter Wiemhöfer. "Disiloxanes with cyclic or non-cyclic carbamate moieties as electrolytes for lithium-ion batteries." Chemical Communications 49, no. 12 (2013): 1190. http://dx.doi.org/10.1039/c2cc38326h.

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13

Caggiano, Lorenzo, John Davies, David J. Fox, David C. Moody, and Stuart Warren. "A novel silica catalysed stereoselective cyclic carbamate and carbonate rearrangement." Chemical Communications, no. 14 (2003): 1650. http://dx.doi.org/10.1039/b303791f.

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14

Williams, Alfred L., Teresa Abad Grillo, and Daniel L. Comins. "A Novel Free-Radical Ring Contraction of a Cyclic Carbamate." Journal of Organic Chemistry 67, no. 6 (2002): 1972–73. http://dx.doi.org/10.1021/jo0163290.

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15

Sakaitani, Masahiro, and Yasufumi Ohfune. "A new mode of cyclic carbamate formation via tert-butyldimethylsilyl carbamate. Stereoselective syntheses of statine and its analogue." Tetrahedron Letters 28, no. 34 (1987): 3987–90. http://dx.doi.org/10.1016/s0040-4039(00)96439-6.

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16

Song, He, Xin Hua Deng, and Qian Li. "Preparation and Study of a New Polyurethane Curing Agent." Applied Mechanics and Materials 204-208 (October 2012): 4075–78. http://dx.doi.org/10.4028/www.scientific.net/amm.204-208.4075.

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A new environmentally friendly polyurethane curing agent was prepared by the method that cyclic carbonate reacted with isophorone diamine. Investigated the synthesis temperature of the curing agent by DSC and FT-IR, and discussed membrane mechanical properties by curing agent and thermal properties of membrane. The results showed cyclic carbonate reacted violently with isophorone diamine in 82 °C, and the carbamate group appeared on molecular chain; breaking strength of the film and given elongation modulus was greatly improved by using this curing agent.

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17

Heggelund, Audun, and Kjell Undheim. "Preparation of cyclic 2′,3′-carbamate derivatives of erythromycin macrolide antibiotics." Bioorganic & Medicinal Chemistry 15, no. 9 (2007): 3266–77. http://dx.doi.org/10.1016/j.bmc.2007.02.028.

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18

Whitehead, Marek W. J., Nikolay Khanzhin, Lubor Borsig, and Thierry Hennet. "Custom Glycosylation of Cells and Proteins Using Cyclic Carbamate-Derivatized Oligosaccharides." Cell Chemical Biology 24, no. 11 (2017): 1336–46. http://dx.doi.org/10.1016/j.chembiol.2017.08.012.

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19

Köll, Peter, József Kovács, Dirk Abeln та Jürgen Kopf. "Crystal and molecular structure of α-d-ribopyranosylamine 1,3-(cyclic carbamate)". Carbohydrate Research 239 (лютий 1993): 245–48. http://dx.doi.org/10.1016/0008-6215(93)84219-v.

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20

Jeschke, Steffen, Ann-Christin Gentschev, and Hans-Dieter Wiemhoefer. "ChemInform Abstract: Disiloxanes with Cyclic or Non-Cyclic Carbamate Moieties as Electrolytes for Lithium-Ion Batteries." ChemInform 44, no. 23 (2013): no. http://dx.doi.org/10.1002/chin.201323169.

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21

Pattarozzi, Mariella, Cristiano Zonta, Quirinus B. Broxterman та ін. "Stereoselective Iodocyclization of (S)-Allylalanine Derivatives: γ-Lactone vs Cyclic Carbamate Formation". Organic Letters 9, № 12 (2007): 2365–68. http://dx.doi.org/10.1021/ol070764k.

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22

Chen, Guihui, Pan Pan, Yun Yao, Ying Chen, Xiangbao Meng, and Zhongjun Li. "Regioselective modification of amino groups in aminoglycosides based on cyclic carbamate formation." Tetrahedron 64, no. 38 (2008): 9078–87. http://dx.doi.org/10.1016/j.tet.2008.07.022.

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23

Heggelund, Audun, Christian Rømming, and Kjell Undheim. "Preparation and antibacterial activity of cyclic 2′,3′-carbamate derivatives of azithromycin." European Journal of Medicinal Chemistry 43, no. 8 (2008): 1657–64. http://dx.doi.org/10.1016/j.ejmech.2007.10.013.

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24

Helm, Richard F., and Joseph J. Karchesy. "A Novel Cyclic Carbamate from the Acid-Catalyzed Reaction ofD-Glucose and Urea." Journal of Carbohydrate Chemistry 8, no. 5 (1989): 687–92. http://dx.doi.org/10.1080/07328308908048030.

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25

Ma, Chenchen, Zhaopeng Liu, Hualong Song, Rentao Jiang, Fawen He, and Shutao Ma. "Synthesis and antibacterial activity of novel 11,12-cyclic carbonate azithromycin 4″-O-carbamate derivatives." Journal of Antibiotics 63, no. 1 (2009): 3–8. http://dx.doi.org/10.1038/ja.2009.108.

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26

Popović-Djordjević, Jelena B., Ivana I. Jevtić, Nadja Dj Grozdanić та ін. "α-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives". Journal of Enzyme Inhibition and Medicinal Chemistry 32, № 1 (2017): 298–303. http://dx.doi.org/10.1080/14756366.2016.1250754.

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27

Knight, John D., and Don M. Coltart. "Asymmetric anti-aldol addition of achiral ketones via chiral N-amino cyclic carbamate hydrazones." Chemical Communications 49, no. 68 (2013): 7495. http://dx.doi.org/10.1039/c3cc44716b.

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28

Ma, Shutao, Ruixin Ma, Zhaopeng Liu, Chenchen Ma, and Xuecui Shen. "Synthesis and antibacterial activity of novel 15-membered macrolide derivatives: 4″-Carbamate, 11,12-cyclic carbonate-4″-carbamate and 11,4″-di-O-arylcarbamoyl analogs of azithromycin." European Journal of Medicinal Chemistry 44, no. 10 (2009): 4010–20. http://dx.doi.org/10.1016/j.ejmech.2009.04.030.

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29

Suzuki, Masato, Atsuhiko Ii, and Takeo Saegusa. "Multibranching polymerization: palladium-catalyzed ring-opening polymerization of cyclic carbamate to produce hyperbranched dendritic polyamine." Macromolecules 25, no. 25 (1992): 7071–72. http://dx.doi.org/10.1021/ma00051a055.

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30

Alsina, Jordi, Francesc Rabanal, Cristina Chiva, Ernest Giralt, and Fernando Albericio. "Active carbonate resins: Application to the solid-phase synthesis of alcohol, carbamate and cyclic peptides." Tetrahedron 54, no. 34 (1998): 10125–52. http://dx.doi.org/10.1016/s0040-4020(98)00606-1.

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31

Knight, John D., Scott J. Sauer, and Don M. Coltart. "Asymmetric Total Synthesis of the Antimalarial Drug (+)-Mefloquine Hydrochloride via ChiralN-Amino Cyclic Carbamate Hydrazones." Organic Letters 13, no. 12 (2011): 3118–21. http://dx.doi.org/10.1021/ol2010193.

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32

Tae, Jinsung, and Leo A. Paquette. "Delineating the possibilities for intramolecular interception of the squarate ester cascade through the use of metalated enecarbamates." Canadian Journal of Chemistry 78, no. 6 (2000): 689–96. http://dx.doi.org/10.1139/v99-235.

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Highly functionalized and annulated 2,4-cyclooctadienones are formed in a stereoselective manner by sequential treatment of squarate esters with a lithiated enecarbamate (six-membered ring or larger) and a cycloalkenyl- or 1-alkenyllithium reagent. The mechanistic details of this multistep process are presented. Particular attention is drawn to the step that involves intramolecular nucleophilic attack by a proximal oxido anion at the carbamate carbonyl and results in redirection of the cascade. This step is thwarted when five-membered cyclic enecarbamates are employed because of the excessive

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33

Knight, John D., and Don M. Coltart. "Expanding the scope of the asymmetric anti-aldol addition of chiral N-amino cyclic carbamate hydrazones." Tetrahedron Letters 54, no. 40 (2013): 5470–72. http://dx.doi.org/10.1016/j.tetlet.2013.07.140.

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34

Ma, Chenchen, Zhaopeng Liu, Hualong Song, Rentao Jiang, Fawen He, and Shutao Ma. "ChemInform Abstract: Synthesis and Antibacterial Activity of Novel 11,12-Cyclic Carbonate Azithromycin 4′′-O-Carbamate Derivatives." ChemInform 41, no. 22 (2010): no. http://dx.doi.org/10.1002/chin.201022179.

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35

BOTELLA, J. M., A. KLAEBE, J. PERIE, and E. MONNIER. "ChemInform Abstract: Aminolysis of Cyclic Carbamate Analogues of Carboxybiotin; Metallic Catalysis and Modelling of Carboxyl Transfer." ChemInform 23, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199240058.

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36

Knight, John D., and Don M. Coltart. "ChemInform Abstract: Asymmetric anti-Aldol Addition of Achiral Ketones via Chiral N-Amino Cyclic Carbamate Hydrazones." ChemInform 44, no. 51 (2013): no. http://dx.doi.org/10.1002/chin.201351024.

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37

Červená, Irena, Jiří Holubek, Emil Svátek, and Miroslav Protiva. "Potential antidepressants: 4-(Aminoalkoxy)thioxanthones." Collection of Czechoslovak Chemical Communications 53, no. 6 (1988): 1307–16. http://dx.doi.org/10.1135/cccc19881307.

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Four different approaches were used for preparing a series of the title compounds. Reactions of the sodium salt of 4-hydroxythioxanthone (V) with dimethylaminoalkyl chlorides gave the ethers VI and VII. Partial demethylation of VII via the carbamate IX afforded the secondary amine VIII. Reactions of the 4-bromobutoxy compound XI with amines resulted in II, XII, and XIII. Reaction of V with 1-chloro-2,3-epoxypropane and the following treatment of the resulting XIV with 2-propanamine gave the amino alcohol XV. The xanthone III was obtained via XVIII similarly like II. The products, especially II

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38

Kiso, Makoto, Masayuki Kitagawa, Hideharu Ishida, and Akira Hasegawa. "Studies on Glycan Processing Inhibitors: Synthesis of N-Acetylhexosamine Analogs and Cyclic Carbamate Derivatives of 1-Deoxynojirimycin." Journal of Carbohydrate Chemistry 10, no. 1 (1991): 25–45. http://dx.doi.org/10.1080/07328309108543888.

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39

Wengryniuk, Sarah E., Daniel Lim та Don M. Coltart. "Regioselective Asymmetric α,α-Bisalkylation of Ketones via Complex-InducedSyn-Deprotonation of ChiralN-Amino Cyclic Carbamate Hydrazones". Journal of the American Chemical Society 133, № 22 (2011): 8714–20. http://dx.doi.org/10.1021/ja202267k.

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40

Darras, Fouad H., Beata Kling, Edgar Sawatzky, Jörg Heilmann, and Michael Decker. "Cyclic acyl guanidines bearing carbamate moieties allow potent and dirigible cholinesterase inhibition of either acetyl- or butyrylcholinesterase." Bioorganic & Medicinal Chemistry 22, no. 17 (2014): 5020–34. http://dx.doi.org/10.1016/j.bmc.2014.06.010.

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41

Motokucho, Suguru, Atsushi Sudo, and Takeshi Endo. "Living cationic ring-opening polymerization of five-membered cyclic dithiocarbonate controlled by neighboring group participation of carbamate group." Journal of Polymer Science Part A: Polymer Chemistry 45, no. 19 (2007): 4459–64. http://dx.doi.org/10.1002/pola.22206.

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42

Knight, John D., and Don M. Coltart. "ChemInform Abstract: Expanding the Scope of the Asymmetric anti-Aldol Addition of Chiral N-Amino Cyclic Carbamate Hydrazones." ChemInform 45, no. 3 (2014): no. http://dx.doi.org/10.1002/chin.201403032.

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43

Köll, Peter, and Arne Lützen. "Resolution of racemic carboxylic and sulfonic acids via D-xylose derived new cyclic carbamate reagents (oxazolidin-2-ones)." Tetrahedron: Asymmetry 6, no. 1 (1995): 43–46. http://dx.doi.org/10.1016/0957-4166(94)00347-e.

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44

More, Ganesh Sunil, and Rajendra Srivastava. "Efficient Activation of CO2 over Ce-MOF-derived CeO2 for the Synthesis of Cyclic Urea, Urethane, and Carbamate." Industrial & Engineering Chemistry Research 60, no. 34 (2021): 12492–504. http://dx.doi.org/10.1021/acs.iecr.1c01759.

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45

H. Ouf, Nabil, Mohamed A.Hamed, Ibrahim El Sayed, and Mohamed Ibrahim Sakran. "Anti-cancer, Anti-inflammatory, Cytotoxic and Biochemical Activities of a Novel Phosphonotripeptide Synthesized from Formyl Pyrazolofuran using TUBU as Condensing Agent." JOURNAL OF ADVANCES IN CHEMISTRY 6, no. 3 (2010): 1093–102. http://dx.doi.org/10.24297/jac.v6i3.2647.

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A novel and mild protocol for the synthesis of phosphonotripeptide 16 were achieved from novel formylpyrazolofuran 3, benzyl carbamate 5, triphenyl phosphite 6 by Birum-Oleksyszyn reaction using copper (II) trifliate as Lewis acid catalyst in dry dichloromethane at room temperature which synthesis of novel N-benzyloxy-α-aminophosphonate 7 . A mechanism for this condensation reaction is proposed. Cleavage of the N-benzyloxy carbonyl group under acid hydrolysis afford the free α-aminophosphonate 9 in quantitative yield. This in turn, by reaction with N-phthaloylglycine 12 via TUBU to phthalimido

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46

Miranda, Margarida S., Paulo J. O. Ferreira, Joaquim C. G. Esteves da Silva, and Joel F. Liebman. "Three-membered ring amides — a calculational and conceptual study of the structure and energetics of 1,2-oxaziridine-3-one and aziridine-2,3-dione." Canadian Journal of Chemistry 93, no. 4 (2015): 406–13. http://dx.doi.org/10.1139/cjc-2014-0321.

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Species with three-membered rings and the amide linkage are well studied. A quick perusal of the literature with SciFinder finds some 50 000 references to cyclopropanes and almost 300 000 references to amides. In the current paper, we discuss the structure and energetics of two understudied three-membered ring amides, 1,2-oxaziridine-3-one (5) (simultaneously describable as the simplest cyclic carbamate and simplest hydroxamate) and aziridine-2,3-dione (7) (simultaneously describable as the simplest imide and simplest α-ketoamide), with but 5 and nearly 10 references, respectively, for these t

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47

KRAWINKLER, K., N. MAIER, E. SAJOVIC, and W. LINDNER. "Novel urea-linked cinchona-calixarene hybrid-type receptors for efficient chromatographic enantiomer separation of carbamate-protected cyclic amino acids." Journal of Chromatography A 1053, no. 1-2 (2004): 119–31. http://dx.doi.org/10.1016/s0021-9673(04)01206-3.

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48

KISO, M., M. KITAGAWA, H. ISHIDA, and A. HASEGAWA. "ChemInform Abstract: Studies on Glycan Processing Inhibitors: Synthesis of N- Acetylhexosamine Analogs and Cyclic Carbamate Derivatives of 1- Deoxynojirimycin." ChemInform 23, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199203310.

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49

Venkatram, Raghunandan, Vasanth Kumar Pai, and Sriharsha Nagaraj. "Stereoselective Synthesis and Dissolution Studies on Enteric Coated Pellets of (S)-Duloxetine Hydrochloride." Journal of Nepal Chemical Society 28 (May 23, 2013): 74–79. http://dx.doi.org/10.3126/jncs.v28i0.8110.

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The enantioselective hydrogenation of 2-bromo-1-(thiophen-2-yl)ethanone and further elaboration of thr cyclic carbamate derived from γ-aminoalcohol to provide a facile synthesis of (S)-duloxetine, a potent dual inhibitor of serotonin and norepinephrine reuptake, is described. Enteric coated pellets with polymer load 25% and 30% failed to provide required acid resistant to the pellets but very insignificant amount of drug was leached from the coated tablets in acid phase with polymer load 35% and 40% in the acidic phase whereas almost the whole amount of drug was released in the buffer phase. T

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50

Nishida, M., T. Kodama, S. Obika, and T. Imanishi. "Synthesis and chemical properties of a novel 2',4'-bridged nucleic acid analogue with a seven-membered cyclic carbamate structure." Nucleic Acids Symposium Series 51, no. 1 (2007): 157–58. http://dx.doi.org/10.1093/nass/nrm079.

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