Selenium-containing heterocycles. Synthesis and reactions of 2-amino-4,5,6,7-tetrahydro-1-benzoselenophene-3-carbonitrile with anticipated biological activity

Abstract

Reaction of 2-amino-4,5,6,7-tetrahydro-1-benzoselenophene-3-carbonitrile with ethylenediamine in the presence of a catalytic amount of carbon disulfide afforded 2-amino-3-(4,5-dihydro-1H-imidazol-2-yl)-4,5,6,7-tetrahydro-1- benzoselenophene. Cyclocondensation of the latter with triethyl orthoformate, benzaldehyde, and carbon disulfide gave tetracyclic imidazobenzoselenophenopyrimidine derivatives. Treatment of 2,3,5,6,8,9,10,11- octahydroimidazo[2,1-c][1]benzoselenopheno[3,2-e]pyrimidine-5-thione with hydrazine hydrate led to the corresponding 5-hydrazino derivative whose reactions with triethyl orthoformate and sodium nitrite were accompanied by closure of 1,2,4-triazole and tetrazole rings, respectively. Fused benzoseleno-phenopyrimidine systems were also obtained by reaction of 2-amino-4,5,6,7-tetrahydrobenzo-1-selenophene-3-carbonitrile with formamide, carbon disulfide, and phenyl isothiocyanate. Some newly synthesized compounds were tested for antimicrobial and antifungal activity. © 2005 Pleiades Publishing, Inc.