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

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posted on 2023-06-08, 16:59 authored by Mark BagleyMark Bagley, Vincenzo Fusillo, Robert L Jenkins, M Caterina Lubinu, Christopher Mason
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.

Funding

EPSRC; GR/S41463

EPSRC; GR/S25456

History

Publication status

  • Published

File Version

  • Published version

Journal

Beilstein Journal of Organic Chemistry

ISSN

1860-5397

Publisher

Beilstein-Institut

Volume

9

Page range

1957-1968

Department affiliated with

  • Chemistry Publications

Full text available

  • Yes

Peer reviewed?

  • Yes

Legacy Posted Date

2014-06-24

First Open Access (FOA) Date

2014-06-24

First Compliant Deposit (FCD) Date

2014-06-24

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