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One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor.


ABSTRACT: The Bohlmann-Rahtz pyridine synthesis and the Hantzsch dihydropyridine synthesis can be carried out in a microwave flow reactor or using a conductive heating flow platform for the continuous processing of material. In the Bohlmann-Rahtz reaction, the use of a Brønsted acid catalyst allows Michael addition and cyclodehydration to be carried out in a single step without isolation of intermediates to give the corresponding trisubstituted pyridine as a single regioisomer in good yield. Furthermore, 3-substituted propargyl aldehydes undergo Hantzsch dihydropyridine synthesis in preference to Bohlmann-Rahtz reaction in a very high yielding process that is readily transferred to continuous flow processing.

SUBMITTER: Bagley MC 

PROVIDER: S-EPMC3817555 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor.

Bagley Mark C MC   Fusillo Vincenzo V   Jenkins Robert L RL   Lubinu M Caterina MC   Mason Christopher C  

Beilstein journal of organic chemistry 20130930


The Bohlmann-Rahtz pyridine synthesis and the Hantzsch dihydropyridine synthesis can be carried out in a microwave flow reactor or using a conductive heating flow platform for the continuous processing of material. In the Bohlmann-Rahtz reaction, the use of a Brønsted acid catalyst allows Michael addition and cyclodehydration to be carried out in a single step without isolation of intermediates to give the corresponding trisubstituted pyridine as a single regioisomer in good yield. Furthermore,  ...[more]

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