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Stereoselective Synthesis of Pyrano[3,2‐ c ]‐ and Furano[3,2‐ c ]quinolines: Samarium Diiodide‐Catalyzed One‐Pot Aza‐Diels–Alder Reactions
Author(s) -
Zhou Zhuqing,
Xu Fan,
Han Xiaoyan,
Zhou Jun,
Shen Qi
Publication year - 2007
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.200700288
Subject(s) - chemistry , stereoselectivity , dihydropyran , catalysis , samarium diiodide , samarium , organic chemistry , diels–alder reaction , medicinal chemistry
Three‐component aza‐Diels–Alder reactions involving aromatic aldehydes, aromatic amines, and dihydropyran or dihydrofuran are effectively catalyzed by samarium diiodide to afford pyrano[3,2‐ c ]‐ or furano[3,2‐ c ]quinolines in good yields and with high stereoselectivities. Either the cis or the trans isomers can be obtained as the major products by conveniently controlling reaction conditions.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)