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An Unusual Route to Synthesize Indolizines through a Domino S N 2/Michael Addition Reaction Between 2‐Mercaptopyridine and Nitroallylic Acetates
Author(s) -
Roy Suparna
Publication year - 2019
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.201801426
Subject(s) - chemistry , yield (engineering) , moiety , domino , michael reaction , cascade reaction , reaction conditions , sulfur , base (topology) , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , mathematical analysis , materials science , mathematics , metallurgy
A straightforward synthesis of indolizines has been demonstrated from the reaction of 2‐mercaptopyridine and nitroallylic acetates in the presence of a base. The products were obtained in good isolated yield under relatively mild reaction conditions. The mechanistic insight of the reaction has been revealed by performing some control experiments demonstrating that the reaction is initiated by a sequential S N 2/Michael addition reaction followed by removal of the sulfur moiety.