Annulations of α‐Carbamoyl Ketene Dithioacetals with Dicarboxylic Acid Dichlorides: Synthesis of Functionalized Pyrrolidinetriones and Piperidinetriones | Zendy

Dong Ying | Zendy; Guo Yaru | Zendy; Liu Jun | Zendy; Zheng Gang | Zendy; Wang Mang | Zendy

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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

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.

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