A Three-Component Ugi-Type Reaction of N-Carbamoyl Imines Enables a Broad Scope Primary α-Amino 1,3,4-Oxadiazole Synthesis

被引：10
|
作者：
Matheau-Raven, Daniel [1 ]
Boulter, Elizabeth [1 ]
Rogova, Tatiana [1 ]
Dixon, Darren J. [1 ]
机构：
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 21期
基金：
英国工程与自然科学研究理事会; 加拿大自然科学与工程研究理事会;
关键词：
IMIDAZOLE-1-SULFONYL AZIDE; DERIVATIVES; NITROGEN; QUANTIFICATION; HETEROCYCLES; DIVERSITY; ALDEHYDES; EFFICIENT; SCALES;
D O I：
10.1021/acs.orglett.1c02945
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general synthesis of N-protected primary alpha-amino 1,3,4-oxadiazoles, from N-carbamoyl imines, N-isocyanimino-triphenylphosphorane (NIITP), and carboxylic acids, is described. Featuring an isocyanide addition reaction with N-carbamoyl imines, this efficient three-component Ugi-type reaction was found to be broad in scope with respect to imine, and carboxylic acid coupling partners. Furthermore, the versatility of this method was demonstrated by alpha-amino 1,2,4-triazole synthesis, the late-stage functionalization of seven drug molecules, and five divergent derivatizations of a primary alpha-amino 1,3,4-oxadiazole.
引用
收藏
页码：8209 / 8213
页数：5
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