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Reductive-cyclization-mediated syntheses of fused polycyclic quinolines from the Baylis-Hillman adducts of acrylonitrile: Scope and limitations

IR@CDRI: CSIR-Central Drug Research Institute, Lucknow

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Field Value
 
Creator Singh, Virender
Hutait, Samiran
Batra, Sanjay
 
Date 2010-03-04T06:15:20Z
2010-03-04T06:15:20Z
2009
 
Identifier Eur. J. Org. Chem. 2009, 3454–3466
http://hdl.handle.net/123456789/524
 
Description Syntheses of a variety of polycyclic quinolines are described. The target molecules were obtained in two steps through initial reductive cyclization succeeded by another intramolecular cyclization in the allyl amines afforded either from the acetates or the allyl bromides of Baylis-Hillman adducts of 2-nitrobenzaldehydes and acrylonitrile. The two steps proceeded in one-pot for the substrates wherein formyl or hydroxyl group reacted with the amino group of 2-aminoquinoline for second intramolecular cyclization. On the contrary, basic medium was necessary for second intramolecular cyclization in the substrates where alkoxycarbonyl group and the amino-group group participated.
 
Format 265287 bytes
application/pdf
 
Language en
 
Relation CDRI Communication Number 7610
 
Subject Baylis-Hillman
Acrylonitrile
Reductive-cyclization
Intramolecular cyclization
Quinoline
Annulation
 
Title Reductive-cyclization-mediated syntheses of fused polycyclic quinolines from the Baylis-Hillman adducts of acrylonitrile: Scope and limitations
 
Type Article