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Application of Japp-Klingemann Reaction in the Synthesis of Azacarbazole Derivatives: Synthesis of 1,8-Disubstituted-2,3-Dihydro-1H-Pyrido[3,2-b]Indol-4- (5H)-Ones from Aryl Amines

Arti Jhanwar, Ruchi Tyagi, Bharti Vashistha, Vidushi Srivastava, Bhawani Singh and D. Kishore

Application of the Japp-Klingemann reaction on N-substituted-(3-hydroxymethylidine)-piperidin- 4-one 2(a-d) and aryldiazonium chloride 1(a-d) yielded 3-aryl hydrazones of N-substituted piperidin-4- ones 3(a-g). Fischer indolization of these hydrazones with Kent’s reagent (4:1 mixture of acetic acid : HCl) afforded 1,8-disubstituted-2,3-dihydro-1H-pyrido[3,2-b]-indol-4-(5H)-ones 4(a-g) in moderate to good yield. Azacarbazole derivatives 4(a-g) were characterized by microanalysis, IR, 1H NMR and MS spectral data.