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Reductive‐Cyclization‐Mediated Synthesis of Fused Polycyclic Quinolines from Baylis–Hillman Adducts of Acrylonitrile: Scope and Limitations
Author(s) -
Singh Virender,
Hutait Samiran,
Batra Sanjay
Publication year - 2009
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.200900336
Subject(s) - chemistry , acrylonitrile , intramolecular force , adduct , baylis–hillman reaction , organic chemistry , medicinal chemistry , stereochemistry , copolymer , polymer
The synthesis of a variety of polycyclic quinolines is described. The target molecules were obtained in two steps by an initial reductive cyclization followed by another intramolecular cyclization in the allylamines afforded from either the acetates or allyl bromides of Baylis–Hillman adducts of 2‐nitrobenzaldehydes and acrylonitrile. The two steps proceeded in one‐pot for those substrates in which a formyl or hydroxy group reacted with the amino group of the 2‐aminoquinoline in the second intramolecular cyclization. In contrast, a basic medium was necessary for the second intramolecular cyclization reaction in substrates in which an alkoxycarbonyl group and the amino group participated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)