Synthesis and Products of the Methylation of 2‐(2‐Furyl)imidazo[4,5‐f]benzimidazole.

Abstract

imidazo[4,5-f]benzimidazole. -The synthesis of title compound (III) is reported for the first time. -(ACHKASOVA, A. A.; MAKSIMOVA, L. N.; EL'CHANINOV, M. M.; LUKYANOV, B. S.; Chem. Heterocycl.

Synthesis of 2-(3-furyl)-1H-benzimidazoles from 2-phenacyl-1H-benzimidazoles

“…2-(2-Furyl)benzimidazole possesses marked antimicrobial activity and has been intensively subject to structural modification by chemists [1][2][3][4][5][6][7][8][9][10]. On the other hand its structural analogs with 3-furyl substituents are little known, only two compounds of this type have been reported.…”

“…The selectivity of C-alkylation with phenacyl bromides, as we have established, depends on the reaction conditions and is reduced on increasing the electron-withdrawing properties of the aryl substituents Ar and Ar′ in the initial reactants. On interacting compounds 1a and 2a in boiling acetone over potassium carbonate (under conditions typical of alkylating with bromoketones), in addition to the desired DMSO-d 6 The desired products 3 were isolated from the reaction mixture in high yield (77-85%) in the majority of examples without contamination by products of N-alkylation and purification was not required. An exception was the alkylation of compound 1d containing the most electron-withdrawing aryl substituent (Ar = 4-BrC 6 H 4 ) in the series of reactants 1 used.…”