Acid-mediated synthesis of fully substituted 1,2,3-triazoles: multicomponent coupling reactions, mechanistic study, synthesis of serine hydrolase inhibitor and its derivatives

被引：23

作者：

Zhang, Huan ^{[1
]}

Tanimoto, Hiroki ^{[1
]}

Morimoto, Tsumoru ^{[1
]}

Nishiyarna, Yasuhiro ^{[1
]}

Kakiuchi, Kiyomi ^{[1
]}

机构：

[1] Nara Inst Sci & Technol NAIST, Grad Sch Mat Sci, Ikoma, Nara 6300192, Japan

来源：

TETRAHEDRON | 2014年 / 70卷 / 52期

关键词：

Organic azides; Multicomponent coupling reactions triazoles; Reaction mechanism; Bioactive compounds; C-BOND-CLEAVAGE; PROPARGYLIC ALCOHOLS; CLICK CHEMISTRY; ORGANIC AZIDES; TRANSANNULATION; REARRANGEMENTS; ANNULATION; TRIAZOLES; LIGANDS;

D O I：

10.1016/j.tet.2014.10.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the full details of multicomponent coupling reactions in acid-mediated synthesis of fully substituted 1,2,3-triazoles syntheses, and their applications to bioactive molecule synthesis. For substitution with wide range of nucleophiles, selection of acids or activating reagents was important, and various types of multicomponent coupling reactions were demonstrated, allowing functionalization with alcohols, amines, thiol, azide, and carbon nucleophiles. Four-component couplings including double triazolations were also tested. The efficiency of this method was demonstrated by the synthesis of serine hydrolase inhibitor and its novel substituted derivatives. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：9828 / 9835

页数：8

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