A facile access to novel spiroxindole fused pyrrolidine and thiazolo pyrrolidine benzimidazole derivatives via 1,3-dipolar cycloaddition reaction

Add time:09/03/2019    Source:sciencedirect.com

A series of benzo[d]imidazol-2-yl)-1′-methyl-2-oxo-4′-phenylspiro[indoline-3,2′-pyrrolidine] and benzo[d]imidazol-2-yl)-2-oxo-7′-phenyl-3′,6′,7′,7a′-tetrahydro-1′H-spiro[indoline-3,5′-pyrrolo[1,2-c]thiazole] carbonitrile were synthesized via 1,3-dipolar cycloaddition (1,3-DC) reaction. The azomethine ylides generated in situ from isatin/N-substituted isatin and secondary amino acids (sarcosine/S-proline) reacted with benzo-imidazol-2-yl-3-phenylacrylonitrile as a dipolarophile to give spiroxindole fused pyrrolidine and thiazolo pyrrolidine benzimidazole derivatives in good yields. The structure and stereochemistry of cycloadducts were confirmed by 1H and 13C NMR spectroscopy, mass spectrometry, and single crystal X-ray diffraction studies.

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