Benzotriazol-1-yl-sulfonyl Azide for Diazotransfer and Preparation of Azidoacylbenzotriazoles

Benzotriazol-1-yl-sulfonyl azide, a new crystalline, stable, and easily available diazotransfer reagent provides N-(α-azidoacyl)benzotriazoles convenient for N-, O-, C- and S-acylations. The efficient syntheses of various amides, azido protected peptides, esters, ketones and thioesters is reported t...

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Bibliographic Details
Published in:Journal of organic chemistry 2010-10, Vol.75 (19), p.6532-6539
Main Authors: Katritzky, Alan R, El Khatib, Mirna, Bol’shakov, Oleg, Khelashvili, Levan, Steel, Peter J
Format: Article
Language:English
Subjects:
Azides - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Molecular Structure
Organic chemistry
Peptides
Preparations and properties
Stereoisomerism
Triazoles - chemical synthesis
Triazoles - chemistry
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Summary:Benzotriazol-1-yl-sulfonyl azide, a new crystalline, stable, and easily available diazotransfer reagent provides N-(α-azidoacyl)benzotriazoles convenient for N-, O-, C- and S-acylations. The efficient syntheses of various amides, azido protected peptides, esters, ketones and thioesters is reported together with a wide range of azides (including α-azido acids from α- amino acids in partially aqueous conditions) and diazo compounds.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo101296s