One-Pot Multicomponent Michael and Thorpe–Ziegler Reaction of Aryl Methyl Ketones

Abstract

A regioselective base-promoted Michael and Thorpe–Ziegler reaction between aryl methyl ketones and α,β-unsaturated nitrile was carried out in a single step. Different functional groups in addition to active positions were tolerated under this condition. Results indicated that the reaction proceeds in a consecutive manner as double Michael, triple Michael, and Thorpe–Ziegler condensation. By applying click chemistry, double Michael adducts were converted to bis-tetrazoles, which have broad applications in coordination and medicinal chemistry.

Graphical Abstract

Keywords:

• Aryl methyl ketone
• tetrazoles
• Thorpe–Ziegler condensation
• triple Michael reaction

ACKNOWLEDGMENTS

The authors are grateful to Dr. P. S. Ahuja, director of the Institute of Himalayan Bioresource Technology, for providing the necessary facilities during the course of the work. Two of the authors, Vikas Jaitak and Bandna, thank the Council of Scientific and Industrial Research, New Delhi, for senior research fellowships.

Notes

^aIsolated yields for pure compounds.

^bX˭NH.

^cX˭O.

IHBT Communication No. 1011.