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Selective Synthesis of 5,6‐Dihydroindolo[1,2‐ a ]quinoxalines and 6,7‐Dihydroindolo[2,3‐ c ]quinolines by Orthogonal Copper and Palladium Catalysis
Author(s) -
Zhang Lei,
Zhao Fei,
Zheng Mingyue,
Zhai Yun,
Wang Jiang,
Liu Hong
Publication year - 2013
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.201300667
Subject(s) - chemistry , palladium , moiety , indole test , intramolecular force , catalysis , copper , adduct , combinatorial chemistry , ugi reaction , medicinal chemistry , isocyanide , organic chemistry
In combination with the Ugi four‐component reaction, two important indole‐fused heterocycles have been prepared in two steps from readily accessible starting materials. From the same set of Ugi adducts 5 , 5,6‐dihydroindolo[1,2‐ a ]quinoxalines 6 were rapidly generated in excellent yields by a copper‐catalyzed N–H arylation pathway, whereas 6,7‐dihydroindolo[2,3‐ c ]quinolones 7 were obtained by palladium‐catalyzed C–H arylations in good yields without the protection of the indole N1 moiety. Microwave heating was used to accelerate these intramolecular C–N and C–C bond‐forming reactions performed under controlled reaction conditions.