Synthesis of indoloquinolones, triazoloindoloquinolines and its derivatives

Abstract

1<i>H</i>,2<i>H</i>-2-Oxo-4-hydrazinoquinolines <b>1a-e</b> on treatment with cyclohexanone give corresponding 1<i>H</i>,2<i>H</i>-2-oxo-4<i>-</i>quinolinylcyclohexanonehydrazones <b>2a-e.</b> Thermal Fischer indolization of <b>2a-e</b> yield 5,6-dihydro-11<i>H</i>-6-oxo-indolo[3,2-<i>c</i>]quinoline <b>3a-e</b>. Chlorination of <b>3a-e</b> affords the corresponding chloro compounds 11<i>H</i>-6-chloroindolo [3,2-<i>c</i>] quinolines <i>4a-e</i>, which on treatment with hydrazine hydrate give 11<i>H</i>-6-indolo [3,2-<i>c</i>] quinolinylhydrazines <b>5a-e</b>. This hydrazone is used as a building block to synthesize corresponding 3-chloro-1<i>'</i>-(11<i>H</i>-indolo[3,2-<i>c</i>]quinolin-6'yl-amino)-4-(4'-nitrophenyl) azetidin-2-ones <b>7a-e</b> and 1-phenyl-8<i>H</i>-indolo[3,2-<i>c</i>]quinolin[3',4': 1,2] triazoles <b>8a-e</b>. <b>1a-e</b> on treatment with <i>p</i>-nitrobenzaldehyde give 4-quinolinylhydrazono-1-4'-nitrophenyl methanes <b>9a-e</b>, which on further treatment with chloroacetyl chloride in triethylamine afford 3-chloro- 1'-(4-quinolin-4'yl-amino)-4-(4'-nitrophenyl)azetidin-2-ones <b>10a-e</b>. Some of these compounds have been screened for their biological activity.