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

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 ad...

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Veröffentlicht in:Beilstein journal of organic chemistry 2013-09, Vol.9 (1), p.1957-1968
Hauptverfasser: Bagley, Mark C, Fusillo, Vincenzo, Jenkins, Robert L, Lubinu, M Caterina, Mason, Christopher
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Sprache:eng
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Zusammenfassung: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.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.9.232