Study on Regioselective Three Component Domino Synthesis of Polyhydrospiro [indoline-3,3’-pyrrolizine]-2-one via [3+2] Cycloaddition Reaction under Ultrasonic-Irradiation

Due to its interesting structure and biological significance, Spiro compounds with attached indole moiety having an all-carbon quaternary stereogenic core have attracted synthetic organic chemists. In present work we have reported synthesis and characterisation of novel Hexahydrospiro [indoline-3,3′-pyrrolizine]-2-one derivatives in good to excellent yields through [3+2] cycloaddtion reaction in regioselective manner under ultrasonic irradiation. Via multicomponent reaction, these compounds were synthesised with substituted 3-cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-one, isatin, L-proline at room temperature. 1H and 13C NMR, IR spectra, mass spectra, and elemental analysis characterised all the synthesised hexahydrospiro molecules. Regioselectivity has also been clarified in synthesised molecules on the basis of secondary orbital interactions. In synthetic chemistry, we have established a very clear and easy approach that has great relevance. This approach provides easy access in a regioselective manner to the new five member heterocyclic frameworks, which are major building blocks of many natural products and could soon become a possible pharmacologically active nucleus.

Author(s) Details

Dr. Vishwa Deepak Tripathi
M. K. College Laheriasarai (A Constituent Unit of Lalit Narayan Mithila University, Darbhanga Bihar), India.

Dr. Anand Mohan Jha
M. L. T. College, Saharsa, (A Constituent Unit of B. N. Mandal University, Madhepura, Bihar), India.

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