The reaction of 2H-2-oxobenzo[b]-pyran-3-hydrazide (2)

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Several new heterocyclic compounds such as benzimidazo[1,2a]piperazine derivatives (5-7;9,10 and 14,15,17) have been synthesized by the reactions of the versatile 2-(1-methyl-1H-benzo[d]imidazol-2-yl)-2-nitrosoacetonitrile (2) with malononitrile derivatives (3a-e) and 2-cyanomethylbenzimidazole derivatives (1b,c). Oxidation of iminopyrazino[1,2a]benzimidazole-3-carbothioamide derivatives 9 via refluxing in aqueous H2O2 solution afforded iminopyrazino[1,2-a]benzimidazole-3-carboamide derivatives

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Several (3) new benzimidazole based polycyclic compounds of potential pharmaceutical interest have been prepared starting from 2‐benzimidazolelyl (1,3‐dioxo‐2‐indenylidene) acetonitrile. Unhypothesized, the C≡N function of the plausible intermediates was released as HCN rather than a classical nucleophilic addition when treated with bidentate reagents such as hydrazines, 5‐amino‐1H‐1,2,4‐triazole, 5‐amino‐4‐cyano‐1H‐pyrazole and 2‐aminobenzimidazole. When compound 3 reacted with active acetonitrile derivatives it afforded new polyfunctional pyridines via elimination of HCN in addition to, new pyrimidine, pyrazine and azepine derivatives.