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Annulations of α‐Carbamoyl Ketene Dithioacetals with Dicarboxylic Acid Dichlorides: Synthesis of Functionalized Pyrrolidinetriones and Piperidinetriones
Author(s) -
Dong Ying,
Guo Yaru,
Liu Jun,
Zheng Gang,
Wang Mang
Publication year - 2014
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.201301227
Subject(s) - ketene , chemistry , annulation , cycloaddition , pyrimidine , dicarboxylic acid , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , stereochemistry
Abstract An annulation strategy based on ketene dithioacetals is described. Under very mild conditions, a number of pyrrolidinetriones 2 and piperidinetriones 3 have been synthesized by the cycloaddition reaction of α‐carbamoyl ketene dithioacetals 1 with di‐carboxylic acid dichlorides in good to excellent yields. Further application of this protocol is highlighted by the synthesis of a set of fused pyrimidine derivatives 4 / 5 from 2 / 3 and amidines.