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, D Kishore
2009 Int. J. Chem. Sci   unpublished
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, 1 H NMR and MS spectral data.
fatcat:52ceh63pprah7eae6tjafhscju