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Unexpected opening of benzimidazole derivatives during 1,3-dipolar cycloaddition |
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| Authors: | Brahim El Azzaoui Mohamadou Lamine Doumbia Heinz Gornitzka |
| Affiliation: | a Laboratoire de Chimie Organique Hétérocyclique, Faculté des Sciences, Université Mohammed V, Avenue Ibn Batouta BP 1014, Rabat, Morocco b Laboratoire d’Hétérochimie Fondamentale et Appliquée, UMR 5069 du CNRS, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex 01, France c Laboratoire de Synthèse et Physicochimie de Molécules d’Intérêt Biologique, UMR 5068 du CNRS, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex 01, France |
| Abstract: | Hydroxylamine hydrochloride adds via a Michael reaction on the acetonylidene moiety of (4Z)-(2-oxopropylidene)-1,2,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one, leading only to 2-[(5-methyl-isoxazol-3-yl)]methyl]benzimidazoles. This report describes the difference of reactivity of C-phenyl-N-phenyl formohydrazonoyl chloride with benzimidazole. For the N-substituted benzimidazole, an unexpected opening of the azole ring occurs, which was confirmed by single crystal X-ray diffraction analysis. |
| Keywords: | Benzimidazole Diphenylnitrilimine 1,3-Dipolar cycloaddition |
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