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Please login to access the full content or check if you have access via Method 4: From Enamines or Imines and [3-(Dimethylamino)allylidene]ammonium Salts

DOI: 10.1055/sos-SD-015-00002

Spitzner, D.Science of Synthesis, (20051568.

[3-(Dimethylamino)allylidene]ammonium salts 228 condense in the presence of a sodium alkoxide with acceptor-stabilized enamines, e.g. ethyl (2E)-3-aminobut-2-enoate (84), or imines (isomerized arylamines) to yield pyridine-3-carboxylates (nicotinates) 229 (Scheme 77).[‌282‌,‌283‌] [3-(Dimethylamino)allylidene]ammonium salt 230 condenses with 1-phenylpropan-1-imine to give the 2,4-bis(dimethylamino)pyridine 231 in 67% yield (Scheme 77).[‌284‌]

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