Selective functional group transformation using guanidine: the conversion of an ester group into an amide in vinylogous ester-aldehydes of imidazole

被引：8
|
作者：
Ujjinamatada, RK [1 ]
Hosmane, RS [1 ]
机构：
[1] Univ Maryland Baltimore Cty, Dept Chem & Biochem, Lab Drug Design & Synth, Baltimore, MD 21250 USA
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 36期
基金：
美国国家卫生研究院;
关键词：
selective conversion; vinylogous ester-aldehyde; vinylogous amide-aldehyde; guanidine;
D O I：
10.1016/j.tetlet.2005.07.024
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and convenient method has been described for the selective conversion of an ester group into the corresponding carboxamide in vinylogous ester-aldehydes of imidazole. The method uses excess guanidine, which protects the aldehyde function as a diaminodihydro-s-triazine moiety. The carboxaldehyde group is regenerated by hydrolysis of the triazine moiety to provide vinylogous amide-aldehydes of imidazole as the final product. (c) 2005 Elsevier Ltd. All rights reserved.
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页码：6005 / 6009
页数：5
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