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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2013
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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. |
format | Online Article Text |
id | pubmed-3817555 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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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