Novel One Pot Regioselective Multicomponent Synthesis of Highly Functionlaized Spiro Pyrrolidines Through 1,3-Dipolar Cycloaddition Approach

Abstract

One-pot multicomponent synthesis of novel highly functionalized spiro pyrrolidine oxindoles has been accomplished in good yields through 1,3-dipolar cycloaddition reaction of azomethine ylide derived from sarcosine and oxindole with various benzimdazole substituted Baylis–Hillman derivatives. The regiochemical and stereochemical outcome of the multicomponent cycloaddition reaction is ascertained by spectroscopic studies, and one of the products was characterized through x-ray crystallographic analysis.

GRAPHICAL ABSTRACT

Keywords:

• Baylis–Hillman
• benzimidazole
• cycloaddition
• imidazole
• spirooxindoles

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Erratum

ACKNOWLEDGMENTS

S. K. thanks the Council of Scientific and Industrial Research for the award of a senior research fellowship. S. K. and R. R. thank the Department of Science and Technology–Funding for Infrastructure in Science and Technology, New Delhi, for the NMR facility.

Notes

^a Isolated products were characterized by ¹H NMR, ¹³C NMR, and mass spectral analysis.

^b Yields refer to pure isolated products after purification by slica-gel column chromatography.

^a Gradually raised when the reaction was conducted.

^b Isolated yield after column chromatography.

^a Isolated products were characterized by ¹H NMR, ¹³C NMR, and mass spectral analysis.

^b Yields refer to pure isolated products after purification by slica-gel column chromatography.