Exocyclic Enamines of Pyrrolo[1,2-a]quinoxalines Generated by 1,3-dipolar Cycloaddition Reactions of Benzimidazolium Ylides to Activated Alkynes
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X Ray
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The reactions of N-acetonylbenzimidazolium chlorides with various activated alkynes, in the presence of bases, led under mild conditions to a mixture of pyrrolo[1,2-a]benzimidazoles (3), 4-methylene-pyrrolo[1,2-a]quinoxaline derivatives (4) and pyrrolo[1,2-a]quinoxalin-4-one derivatives (5). The exocyclic enamine derivatives 4 have been fully characterized by multinuclear NMR spectroscopy and X-ray crystallography. A mechanism rationalizing the formation of the enamine derivatives is proposed.