Isothiourea-catalyzed synthesis of pyrrole- and indole-functionalized tetrasubstituted pyridines

Zhang, Shuyue; Hartley, Will; Greenhalgh, Mark David; Ng, Sean; Slawin, Alexandra Martha Zoya; Smith, Andrew David

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Date

18/09/2020

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Abstract

The generation of pyrrole- and indole-functionalized tetrasubstituted pyridines in a one-pot process from 2-(pyrrol-1-yl)acetic acid or 2-(indol-1-yl)acetic acid and α,β-unsaturated N-sulfonyl-ketimines is described. The process is proposed to operate via an isothiourea-catalyzed Michael addition-lactamization, followed by elimination of sulfinic acid and O-acylation to provide the final pyridine product.

Citation

Zhang , S , Hartley , W , Greenhalgh , M D , Ng , S , Slawin , A M Z & Smith , A D 2020 , ' Isothiourea-catalyzed synthesis of pyrrole- and indole-functionalized tetrasubstituted pyridines ' , ChemCatChem , vol. 12 , no. 18 , pp. 4522-4525 . https://doi.org/10.1002/cctc.202000882

Publication

ChemCatChem

Status

Peer reviewed

DOI

https://doi.org/10.1002/cctc.202000882

ISSN

1867-3880

Type

Journal article

Rights

Copyright © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

Description

Funding: Engineering and Physical Sciences Research Council (Grant Number(s): EP/L016419/1); FP7 Ideas: European Research Council (Grant Number(s): 279850)

Collections

University of St Andrews Research

URI

http://hdl.handle.net/10023/20307