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.

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

Bucciol, Fabio
First
;
Maffeis, Elia;Calcio Gaudino, Emanuela;Jicsinszky, László;Tagliapietra, Silvia;Barge, Alessandro;Prandi, Cristina;Cravotto, Giancarlo
2021-01-01

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.
2021
10
9
1084
1093
Doxycycline; microwave-assisted reaction; cyclodextrins complexation; rhodium catalyst; stereoselective synthesis
Bucciol, Fabio; Maffeis, Elia; Calcio Gaudino, Emanuela; Jicsinszky, László; Tagliapietra, Silvia; Barge, Alessandro; Prandi, Cristina; Cravotto, Gian...espandi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/1801590
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