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A new series of tetrahydroindeno [1, 2-b] pyrrole-3-carboxylate derivatives (4) were synthesized by reaction of 5-amino-2-mercapto benzimidazole with 1, 3-dicarbonyls and activated carbonyl compounds using ceric ammonium nitrate catalyst by a three component one-pot reaction. Structures of these compounds were established on the basis of infrared spectroscopy, proton nuclear magnetic resonance, carbon-13 nuclear magnetic resonance, mass spectrometry and elemental analyses. The title compounds 4a-h were evaluated for antiinflammatory activity using the carrageenan-induced paw edema method at a dose of 100 mg/kg in comparison to ibuprofen as a reference drug. Compounds 4a, 4b, 4c and 4d exhibited potent antiinflammatory activity comparable to that of ibuprofen.