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Convenient synthesis of 2,2-Dimethyl-3,4-dihydro-2 H-pyrano[2,3- b]quinolines

DRS at CSIR-National Institute of Oceanography

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Title Convenient synthesis of 2,2-Dimethyl-3,4-dihydro-2 H-pyrano[2,3- b]quinolines
 
Creator Parsekar, S.B.
Amonkar, C.P.
Parameswaran, P.S.
Tilve, S.G.
 
Subject chemical extraction
Balfourodendron riedelianum
alkaloids
Wittig reaction
 
Description A convenient general synthesis of 2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]quinolines using the Wittig reaction is described. The o-nitrobenzaldehydes (1a-d) on reaction with phosphorane 2 provided (E)-ethyl-a-(2,2-dimethylprop-2-ene)-2-nitrocinnamates (3a-d) in excellent yields, which on cyclization with polyphosphoric acid followed by reductive cyclization using Fe/HCl afforded dihydropyranoquinolines (5a-d). Alternatively, the pyranoquinolines 5a-d were also synthesised from esters 3a-d by employing domino reductive cyclization in a single step
 
Date 2010-11-29T06:43:56Z
2010-11-29T06:43:56Z
2010
 
Type Journal Article
 
Identifier Synthetic Communications, vol.40(21); 3251-3258
http://drs.nio.org/drs/handle/2264/3739
 
Language en
 
Rights The final and definitive form of the preprint has been published in the "Synthetic Communications" © 2010 Taylor & Francis; "Synthetic Communications" is available online at http://www.informaworld.com/ with open URL of artilce : http://www.informaworld.com/smpp/content~db=all?content=10.1080/00397910903398668
 
Publisher Taylor & Francis