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

Autor:	YiHan Tang, Changsheng Yao, Kun Wang, Xinyu Lyu, Hai-Tao Yang, Hong-Rong Guan, Chun-Bao Miao, Wen-Long Ren
Rok vydání:	2021
Předmět:	Pyrazine Chemistry education Organic Chemistry Quinoline Regioselectivity Biochemistry Medicinal chemistry humanities Pyridazine chemistry.chemical_compound Aminolysis Pyridine Michael reaction Pyrrolidinones Physical and Theoretical Chemistry
Zdroj:	Organic Letters. 23:8699-8704
ISSN:	1523-7052 1523-7060
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::48033b44bbea370ef2bed69e3053a4e9 https://doi.org/10.1021/acs.orglett.1c03078 Zobrazit plný text záznamu