Copper-Catalyzed Bisannulations of Malonate-Tethered O‑Acyl Oximes with Pyridine, Pyrazine, Pyridazine, and Quinoline Derivatives for the Construction of Dihydroindolizine-Fused Pyrrolidinones and Analogues

A copper-catalyzed bisannulation reaction of malonate-tethered O-acyl oximes with pyridine, pyrazine, pyridazine, and quinoline derivatives has been developed for the concise synthesis of structurally novel dihydroindolizine-fused pyrrolidinones and their analogues. The present reaction shows excell...

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Bibliographic Details
Published in:Organic letters 2021-11, Vol.23 (22), p.8699-8704
Main Authors: Miao, Chun-Bao, Guan, Hong-Rong, Tang, YiHan, Wang, Kun, Ren, Wen-Long, Lyu, Xinyu, Yao, ChangSheng, Yang, Hai-Tao
Format: Article
Language:English
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Summary:A copper-catalyzed bisannulation reaction of malonate-tethered O-acyl oximes with pyridine, pyrazine, pyridazine, and quinoline derivatives has been developed for the concise synthesis of structurally novel dihydroindolizine-fused pyrrolidinones and their analogues. The present reaction shows excellent regioselectivity and stereoselectivity. Theoretical calculations reveal that the coordination effect of the carbonyl group in the nucleophilic substrate determines the excellent regioselectivity. Further functionalization of the generated dihydroindolizine-fused pyrrolidinone could be easily realized through substitution, Michael addition, selective aminolysis, and hydrolysis reactions.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03078