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

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    Synthetic_ Commun_40_3251a.pdf (99.87Kb)
    Date
    2010
    Author
    Parsekar, S.B.
    Amonkar, C.P.
    Parameswaran, P.S.
    Tilve, S.G.
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    Abstract
    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
    URI
    http://drs.nio.org/drs/handle/2264/3739
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