Premium
A New Facet of Azatriene Reactivity: A Short Cut to 5‐Amino‐3‐methyl‐4‐(1 H ‐pyrrol‐1‐yl)thiophene‐2‐carboxylates and 5‐Amino‐3‐methyl‐4‐(1 H ‐pyrrol‐1‐yl)thiophene‐2‐carbonitriles
Author(s) -
Nedolya Nina A.,
Tarasova Olga A.,
Albanov Alexander I.,
Trofimov Boris A.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800268
Subject(s) - chemistry , thiophene , pyrrole , allene , alkyl , sulfanyl , reactivity (psychology) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
An simple and expedient approach to highly functionalized tetrasubstituted thiophenes from readily accessible starting materials [(1 H ‐pyrrol‐1‐yl)allene, isothiocyanates, and alkyl 2‐bromoacetates or 2‐bromoacetonitrile] has been developed. The method is based on the one‐pot synthesis and fast in‐situ cyclization of alkyl 2‐{[2‐(1 H ‐pyrrol‐1‐yl)buta‐2,3‐dienimidoyl]sulfanyl}acetates or cyanomethyl 2‐(1 H ‐pyrrol‐1‐yl)buta‐2,3‐dienimidothioates (1‐aza‐1,3,4‐trienes) to give previously unknown thiophene‐2‐carboxylates and thiophene‐2‐carbonitriles, respectively, both bearing pyrrole substituents.