1-Acyloxyaziridine-2,2-dicarboxylic acid esters

Мищенко, А. И.; Prosyanik, A. V.; Belov, P. N.; Romanchenko, V. A.; Belova, E. G.; Марков, В. И.

doi:10.1007/bf00515636

Cited by 2 publications

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“…27 Several analogues of COMU have been reported to provide improved peptide couplings, most notably based on oximes 11 (derived from Meldrum's acid) 28 and 12 (derived from dimethylbarbituric acid), 29 which were also included in our studies. Oximes 6, 10-12 or the corresponding silver salts of 8 and 9, were converted to benzoylated derivatives 13, 14, 15, 26 16, 30 17 and 18 by treatment with benzoic anhydride (Bz 2 O) in ether, or using BzCl and pyridine or Et 3 N. Among these examples, we highlight the exceptionally simple preparation of benzoyl-Oxyma (13): addition of Bz 2 O to a 0.3 M solution of Oxyma in Et 2 O resulted in the formation of a precipitate within 1 min. Filtration and drying provided the pure reagent.…”

Section: Design and Synthesis Of Oxime-based Benzoylating Reagentsmentioning

confidence: 99%

Investigation of benzoyloximes as benzoylating reagents: benzoyl-Oxyma as a selective benzoylating reagent

et al. 2016

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Hydroxybenzotriazole (HOBt) and HOBt-derived reagents have been classified as Class I explosives, with restrictions on their transportation and storage. We explored a range of benzoylated oxime-based reagents as alternatives to benzoyloxybenzotriazole (BBTZ) for the selective benzoylation of carbohydrate polyols. Benzoylated oximes derived from 2-hydroximino-malononitrile, ethyl 2-hydroximino-2-cyanoacetate (Oxyma), and tert-butyl 2-hydroximino-2-cyanoacetate were most effective for benzoylation of a simple primary alcohol, with yields approaching that obtained for BBTZ. When applied to carbohydrate diols, the most effective reagent was identified as benzoyl-Oxyma. Benzoyl-Oxyma is a highly crystalline, readily prepared alternative to BBTZ, useful in the selective benzoylation of carbohydrate polyols.

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Section: Design and Synthesis Of Oxime-based Benzoylating Reagentsmentioning

confidence: 99%

Investigation of benzoyloximes as benzoylating reagents: benzoyl-Oxyma as a selective benzoylating reagent

et al. 2016

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Facile and Exclusive Formation of Aziridinofullerenes by Acid-catalyzed Denitrogenation of Triazolinofullerenes

et al. 2012

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Variously substituted [6,6]closed aziridinofullerenes were exclusively obtained from acid-catalyzed denitrogenation of triazolinofullerenes without formation of relevant [5,6]open azafulleroids, which are the major products on noncatalyzed denitrogenation. The mechanistic consideration by DFT calculations suggested a reaction sequence involving initial pre-equilibrium protonation of the triazoline N(1) atom, generation of aminofullerenyl cation by nitrogen-extrusion, and final aziridination.

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1-Acyloxyaziridine-2,2-dicarboxylic acid esters

Cited by 2 publications

References 1 publication

Investigation of benzoyloximes as benzoylating reagents: benzoyl-Oxyma as a selective benzoylating reagent

Investigation of benzoyloximes as benzoylating reagents: benzoyl-Oxyma as a selective benzoylating reagent

Facile and Exclusive Formation of Aziridinofullerenes by Acid-catalyzed Denitrogenation of Triazolinofullerenes

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