Method to build 2,4-substituted selenazole from β-azido diselenide and carboxylic acid: A formal synthesis of selenazofurin

被引：12

作者：

Qiao, Junfei ^{[1
,2
]}

Liu, Yi ^{[3
]}

Du, Yuguo ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Res Ctr Ecoenvironm Sci, State Key Lab Environm Chem & Ecotoxicol, Beijing 100085, Peoples R China

[2] Univ Chinese Acad Sci, Sch Chem & Chem Engn, Beijing 100049, Peoples R China

[3] Yantai Univ, Sch Chem & Chem Engn, Yantai 264005, Peoples R China

来源：

TETRAHEDRON | 2018年 / 74卷 / 24期

关键词：

ORGANOSELENIUM COMPOUNDS; SELENIUM; DERIVATIVES; TIAZOFURIN;

D O I：

10.1016/j.tet.2018.05.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel approach for the synthesis of 2,4-disubstituted selenazoles using carboxylic acids (or anhydrides) and beta-azido diselenide was achieved via a one-pot cascade formation of selenazoline (Staudinger reduction/diselenide cleavage/selenocarbonylation/aza-Wittig reaction) and a following MnO2-promoted oxidation. This method offers excellent substrate flexibility, and its valuable application is exemplified by an efficient total synthesis of Selenazofurin which exhibited good antitumor activities against K562 and A549 cells. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：3061 / 3068

页数：8

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