Abstract A regio- and diastereoselective synthesis of library of structurally intriguing novel hybrid heterocycles comprising spiropyrrolizidines/pyrrolothiazoles, oxindole/acenaphthenone and β-lactam moieties have been synthesized in good yields. The hitherto unexplored 2-((1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl)methylene) malononitriles were used as the dipolarophiles, while the dipoles were derived in situ from indoline-2,3-dione/acenaphthenequinone and l -proline/substituted 2-aryl-thiazolidine-4-carboxylic acids. The key step of this transformation is the 1,3-dipolar cycloaddition reaction involving the above-mentioned components offering a facile entry to biologically relevant classes of spiro heterocyclic hybrids.