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One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor
journal contribution
posted on 2023-06-08, 16:59 authored by Mark BagleyMark Bagley, Vincenzo Fusillo, Robert L Jenkins, M Caterina Lubinu, Christopher MasonThe 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 ChemistryISSN
1860-5397Publisher
Beilstein-InstitutExternal DOI
Volume
9Page range
1957-1968Department affiliated with
- Chemistry Publications
Full text available
- Yes
Peer reviewed?
- Yes