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Modular synthesis of pyrrolo[2,1‐ b ]thiazoles and related monocyclic pyrrolo structures
Author(s) -
O'Dwyer Emma E.,
Mullane Nessa S.,
Smyth Timothy P.
Publication year - 2011
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.550
Subject(s) - chemistry , synthon , isomerization , reductive amination , derivative (finance) , stereochemistry , amination , combinatorial chemistry , modular design , organic chemistry , catalysis , computer science , financial economics , economics , operating system
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).