Microwave-Assisted, One-Pot Synthesis of Doxycycline under Heterogeneous Catalysis in Water

Abstract

The selective synthesis of active pharmaceutical molecules is a challenging issue, particularly when attempting to make the reactions even more sustainable. The present work focuses on the microwave-assisted hydrogenolysis of oxytetracycline to selectively produce α-doxycycline. Although the combination of microwave irradiation and a heterogeneous rhodium catalyst provided good conversions, the selective synthesis of active α-doxycycline was only achieved when an oxytetracycline-cyclodextrin complex was used as the starting material, giving the desired product at 34.0% yield in a one-step reaction under very mild conditions.

Keywords

• doxycycline
• microwave-assisted reaction
• cyclodextrins complexation
• rhodium catalyst
• stereoselective synthesis