Synthesis of Baylis–Hillman-Derived Phosphonated 3-(Benzylaminomethyl)coumarins

Abstract

Treatment of Baylis–Hillman-derived 3-(chloromethyl)coumarins with benzylamine has afforded benzylamino derivatives, sequential chloroacetylation and Michaelis–Arbuzov phosphonation of which have provided access to a series of phosphonate esters as potential HIV-1 protease inhibitors.

Keywords:

• Amides
• Baylis–Hillman
• coumarins
• Michaelis–Arbuzov phosphonation

ACKNOWLEDGMENTS

The authors thank the Medical Research Council of South Africa (MRC), the National Research Foundation (NRF: GUN 2069255), and Rhodes University for generous bursary and financial support. Miss Yi-Chen Lee's assistance with the collection of some of the NMR data is gratefully acknowledged.