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

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 combina...

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Bibliographic Details
Main Authors: Fabio Bucciol, Elia Maffeis, Emanuela Calcio Gaudino, László Jicsinszky, Silvia Tagliapietra, Alessandro Barge, Cristina Prandi, Giancarlo Cravotto
Format: Article
Language:English
Published: MDPI AG 2021-09-01
Series:Antibiotics
Subjects:
Online Access:https://www.mdpi.com/2079-6382/10/9/1084
Description
Summary: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.
ISSN:2079-6382