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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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Autores principales: Bagley, Mark C, Fusillo, Vincenzo, Jenkins, Robert L, Lubinu, M Caterina, Mason, Christopher
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817555/
https://www.ncbi.nlm.nih.gov/pubmed/24204407
http://dx.doi.org/10.3762/bjoc.9.232
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author Bagley, Mark C
Fusillo, Vincenzo
Jenkins, Robert L
Lubinu, M Caterina
Mason, Christopher
author_facet Bagley, Mark C
Fusillo, Vincenzo
Jenkins, Robert L
Lubinu, M Caterina
Mason, Christopher
author_sort Bagley, Mark C
collection PubMed
description 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.
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spelling pubmed-38175552013-11-07 One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor Bagley, Mark C Fusillo, Vincenzo Jenkins, Robert L Lubinu, M Caterina Mason, Christopher Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2013-09-30 /pmc/articles/PMC3817555/ /pubmed/24204407 http://dx.doi.org/10.3762/bjoc.9.232 Text en Copyright © 2013, Bagley et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Bagley, Mark C
Fusillo, Vincenzo
Jenkins, Robert L
Lubinu, M Caterina
Mason, Christopher
One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor
title One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor
title_full One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor
title_fullStr One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor
title_full_unstemmed One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor
title_short One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor
title_sort one-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817555/
https://www.ncbi.nlm.nih.gov/pubmed/24204407
http://dx.doi.org/10.3762/bjoc.9.232
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