Annulations of α‐Carbamoyl Ketene Dithioacetals with Dicarboxylic Acid Dichlorides: Synthesis of Functionalized Pyrrolidinetriones and Piperidinetriones. Issue 4 (28th November 2013)

• Record Type: Journal Article
• Authors: Dong, Ying; Guo, Yaru; Liu, Jun; Zheng, Gang; Wang, Mang
• Is Part Of: European journal of organic chemistry. Issue 4(2014)
• Page Start: 797
• Page End: 801
• Publication Date: 2013-11-28
• Subjects: Synthetic methods -- Nitrogen heterocycles -- Annulation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201301227
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: An annulation strategy based on ketene dithioacetals is described. Under very mild conditions, a number of pyrrolidinetriones2 and piperidinetriones3 have been synthesized by the cycloaddition reaction of α‐carbamoyl ketene dithioacetals1 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 derivatives4 /5 from2 /3 and amidines. Abstract : The cyclization reactions of α‐carbamoyl ketene dithioacetals with dicarboxylic acid dichlorides have been described. The utility of the cyclization products has been demonstrated in the synthesis of 6 H ‐pyrrolo[3, 4‐ d ]pyrimidine‐5, 7‐diones, and pyrido[4, 3‐ d ]pyrimidine‐5, 7(6 H, 8 H )‐diones in concise steps and excellent yields.