The Aza-Prins Reaction of 1,2-Dicarbonyl Compounds with 3-Vinyltetrahydroquinolines: Application to the Synthesis of Polycyclic Spirooxindole Derivatives

Autor:	Yusuke Yoshigoe, Rei Tsukazaki, Shinichi Saito, Tomohiro Katamura, Yuichiro Mutoh, Akito Fujisawa
Jazyk:	angličtina
Rok vydání:	2021
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Enantiopure drug chemistry Isatin Organic Chemistry Diastereomer Organic chemistry Stereoselectivity Prins reaction Benzazocine Article Tricyclic
Zdroj:	The Journal of Organic Chemistry
ISSN:	1520-6904 0022-3263
Popis:	The aza-Prins reaction of 6,7-dimethoxy-3-vinyl-1,2,3,4-tetrahydroquinoline (1) with 1,2-dicarbonyl compounds proceeded smoothly in the presence of HCl, and the corresponding tricyclic benzazocines were isolated in yields of 20-86%. The reaction proceeded in a stereoselective manner, and the formation of the 2,4-trans isomer was observed. The reaction of 1 with an enantiopure ketoester gave the corresponding tricyclic benzazocine as a mixture of diastereomers. The diastereomers were easily separated and converted to enantiopure tricyclic benzazocines. The synthesis of spirooxindole derivatives was achieved by the reaction of 1 with isatin derivatives.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::03aabc9281566c7f2a9d82e9cbe60f0a http://europepmc.org/articles/PMC8650011 Zobrazit plný text záznamu