Synthesis of Benzimidazolyl derivateves of Indoloindole and Benzopyrroloindole

Author: tamar shonia
Co-authors: Sh. Samsonia, M. Trapaidze
Keywords: benzimidazole, benzopyrroloindole, indoloindole, condensation, cyclization
Annotation:

The present Master’s Thesis is devoted to synthesis of new polycyclic heterocyclic compounds benzimidazolylbenzopyrroloindole and benzimidazolylindoloindole. We synthesized dicarboxylic acid of benzo[e]pyrrolo[3,2-g]indole and mono- and di-formyl derivatives of indolo[7,6-g]indole, which were the key compounds. The condensation reaction of dicarboxylic acid of benzo[e]pyrrolo[3,2-g]indole with o-phenylenediamine was carried out in polyphosporic acid and POCl3 area. The probable structure of product which was prepared by condensation and simultaneous cyclization is 2,9-bis(imidazole-2-yl)benzo[e]pirrolo[3,2-g]indole. Condensation and simultaneous cyclization reactions of 3-formyl-1H,6,H-indolo[7,6-g]indole and 3,8-diformyl-1H,6H-indolo[7,6-g]indole with o-phenylenediamine was performed in polyphosphoric acid, glacial acetic acid and POCl3 area. As a result, respectively 3(benzimidazol-2-yl)-1H,6H-indolo[7,6-g]indole and 3,8-bis(benzimidazol-2-yl)-1H,6H-indolo[7,6-g]indole was synthesized. In present work earlier by T. Shonia synthesized bis-spiro compound – bis-(6-brom-2-chromen-2-spiro)- 1’,1’,3’,8’,10’,10’–hexamethylindolino[4,5–e]indoline’s proton magnetic resonance spectrum and mass-spectrum is represented, by which the symmetrical structure of these compound is confirmed. For synthesized compounds IR, UV and proton magnetic resonance spectra is taken, which doesn’t oppose represented structures.