Convenient synthesis of 2,2-Dimethyl-3,4-dihydro-2 H-pyrano[2,3- b]quinolines
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Date
2010Author
Parsekar, S.B.
Amonkar, C.P.
Parameswaran, P.S.
Tilve, S.G.
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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
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