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Modular synthesis of pyrrolo[2,1-b]thiazoles and related monocyclic pyrrolo structures

✍ Scribed by Emma E. O'Dwyer; Nessa S. Mullane; Timothy P. Smyth

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
318 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A modular synthesis of selectively‐substituted pyrrolo[2,1‐b]thiazoles (Δ^6^ isomeric form) has been implemented, involving a distinctive bicyclization reaction of a mucobromic acid derivative followed by a Suzuki‐Miyaura coupling. A novel process of Δ^6^ to Δ^7^ isomerization of the pyrrolothiazole structure was uncovered that appears to involve a 1,4‐addition‐1,2‐elimination mechanism. Preparation of 1,5‐dihydropyrrol‐2‐one structures, selectively substituted at the 3‐ and 4‐positions, was also achieved using the mucobromic acid synthon in a reductive amination process. J. Heterocyclic Chem., (2011).

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