113802-62-3Relevant academic research and scientific papers
Indolobenzodiazepine Derivatives
Hiremath, Shivayogi P.,Badami, Prema S.,Hiremath, Dakshayani M.,Purohit, Muralidhar G.
, p. 522 - 525 (2007/10/02)
Various substituted 3-hydrazino-2-phenylindoles (4a-d) have been synthesised from 3-amino-2-phenylindoles (3a-d) by treatment with HCl and N2H4 at 5-10 deg C.These indoles (4a-d) on condensation with formamide give the corresponding 3-(N2-formyl)hydrazino-2-phenylindoles (5a-d) which undergo acid cyclization furnishing the indolobenzodiazepines (6a-d), a hitherto unknown ring system.These diazepines have also been prepared from 2-phenylindoles by another route. 3-Hydrazino-2-phenylindoles (4a-d) undergo condensation with ethyl chloroformate in pyridine to yield ethyl 2-phenylindole-3-carbazates (7a-d) which are converted into tetrahydroindolobenzodiazepin-5-ones (8a-d) by refluxing in diphenyl ether.LAH reduction of 5,6,7,12-tetrahydroindolobenzodiazepin-5-one (8a) and 5,6,7,14-tetrahydrobenzoindolobenzodiazepin-5-one (8d) yields the corresponding benzodiazepines (9a and 9d), which on dehydrogenation with chloranil in xylene furnish 6a and 6d respectively, identical in all respects with those obtained by the first route.
