One-pot synthesis of pyrroles using a titanium-catalyzed multicomponent coupling procedure

被引：20

作者：

Pasko, Cody M. ^{[1
]}

Dissanayake, Amila A. ^{[1
]}

Billow, Brennan S. ^{[1
]}

Odom, Aaron L. ^{[1
]}

机构：

[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

来源：

TETRAHEDRON | 2016年 / 72卷 / 09期

基金：

美国国家科学基金会;

关键词：

Pyrrole; Catalysis; Multicomponent reaction; Titanium; ETA(1)-PYRROLYL COMPLEXES; IMINE METATHESIS; HYDROAMINATION; N; N-DI(PYRROLYL-ALPHA-METHYL)-N-METHYLAMINE; REACTIVITY; LIGANDS; AMINES;

D O I：

10.1016/j.tet.2016.01.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple one-pot procedure for the production of 2-carboxylpyrroles with 4-alkyl, 5-alkyl, 4-aryl, 4-aryl 5-alkyl, or 3,4-diaryl substitution patterns is presented. The procedure involves the titanium-catalyzed multicomponent coupling of alkynes, primary amines and isonitriles to give 1,3-diimines in situ; the multicomponent product is then treated with the ethyl ester of glycine hydrochloride to give the NH-pyrrole. The reaction can be carried out with the neutralized glycine ester or with the hydrochloride salt using DBU as a base. Yields of pyrrole based on starting alkyne varied from 25 to 65% over the one pot procedure, and in most cases only one regioisomer of the product is observed. Further, it is proposed that the regioselectivities of the reactions are a result of rate-determining ring closure after relatively fast transimination with glycine ethyl ester. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：1168 / 1176

页数：9

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