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2-arylidene-1,3-indanediones undergo a regioselective 1,3-dipolar cycloaddition reaction with the azomethine ylide derived from isatin and proline to give a rare class of novel complex dispirooxindolopyrrolizidines in better yield under microwave irradiation than classical heating. X-ray crystal structure analysis of one of the product confirms the structure and regiochemical outcome of the cycloaddition reaction. Anti-microbial activity studies were carried out with all the newly synthesized dispiro-oxindolopyrrolizidines.