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

Bagley, Mark C, Fusillo, Vincenzo, Jenkins, Robert L, Lubinu, M Caterina and Mason, Christopher (2013) One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor. Beilstein Journal of Organic Chemistry, 9. pp. 1957-1968. ISSN 1860-5397

[img]
Preview
PDF - Published Version
Available under License Creative Commons Attribution.

Download (483kB) | Preview

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.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry
Depositing User: Catrina Hey
Date Deposited: 24 Jun 2014 10:11
Last Modified: 07 Mar 2017 07:45
URI: http://sro.sussex.ac.uk/id/eprint/49047

View download statistics for this item

📧 Request an update
Project NameSussex Project NumberFunderFunder Ref
UnsetUnsetEPSRCGR/S41463
UnsetUnsetEPSRCGR/S25456