Synthesis of hydrazine and azapeptide derivatives by alkylation of carbazates and semicarbazones

被引：22

作者：

Garcia-Ramos, Yesica ^{[1
]}

Proulx, Caroline ^{[1
]}

Lubell, William D. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 2012年 / 90卷 / 11期

基金：

加拿大自然科学与工程研究理事会; 加拿大健康研究院;

关键词：

carbazate; tetraethylammonium hydroxide; semicarbazone; alkylation; fluorenone hydrazine; DIMETHYL-SULFOXIDE; PEPTIDE-SYNTHESIS; AZA-PEPTIDE; CHEMISTRY; ACIDS; ACIDITIES; SOLVENT; GLYCINE; BASES; DKP;

D O I：

10.1139/v2012-070

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hydrazine and azapeptide analogs were synthesized effectively by alkylation of alkylidene carbazates and semicarbazones. In comparisons of benzylidene, benzhydrylidene, and fluorenylidene tert-butyl carbazates in alkylations using bases of different pK(b) character, superior conversion was obtained using the fluorenone derivative. Mild alkylation conditions were found employing Et4NOH as base and used to convert fluorenylidene tert-butyl carbazate into 13 different protected hydrazines. Moreover, racemization was avoided during alkylation of fluorenylidene semicarbazide in the synthesis of aza-propargylglycinylphenylalanine tert-butyl ester, the protecting groups from which could be selectively removed.

引用

页码：985 / 993

页数：9

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