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Isothiourea‐Catalyzed Synthesis of Pyrrole‐ and Indole‐Functionalized Tetrasubstituted Pyridines
Author(s) -
Zhang Shuyue,
Hartley Will C.,
Greenhalgh Mark D.,
Ng Sean,
Slawin Alexandra M. Z.,
Smith Andrew D.
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202000882
Subject(s) - chemistry , pyrrole , pyridine , catalysis , sulfinic acid , acylation , indole test , acetic acid , sulfonyl , organic chemistry , combinatorial chemistry , medicinal chemistry , alkyl
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.