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3-Dimethylamino-2-(1H-indole-3-carbonyl)acrylonitrile (2) was treated with phenylhydrazine, in refluxing basic ethanol, afforded a single product N-1 or N-2 substituted pyrazole. Basic promoted cyclization of enaminonitrile 2 with α-heteroarylamines as N,N-1,3-dinucleophiles, condensed indolylpyrimidines as a new class of meridianine natural product analogs were obtained in moderate to good yields.

arkivoc

Application of (2Z)-3-dimethylamino-2-(1H-indole-3-carbonyl) acrylonitrile in the synthesis of novel 3-heteroarylindoles: condensed meridianine analogs