Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes

In the presence of p-toluenesulfonic acid as catalyst the domino reaction of arylamines, methyl propiolates and aromatic aldehydes in ethanol proceeded smoothly to give polysubstituted 1,2,3,4-tetrahydroquinolines in moderate yields. The reaction is believed to involve the Povarov reaction of in sit...

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Autores principales: Sun, Jing, Gao, Hong, Wu, Qun, Yan, Chao-Guo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3511020/
https://www.ncbi.nlm.nih.gov/pubmed/23209520
http://dx.doi.org/10.3762/bjoc.8.211
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author Sun, Jing
Gao, Hong
Wu, Qun
Yan, Chao-Guo
author_facet Sun, Jing
Gao, Hong
Wu, Qun
Yan, Chao-Guo
author_sort Sun, Jing
collection PubMed
description In the presence of p-toluenesulfonic acid as catalyst the domino reaction of arylamines, methyl propiolates and aromatic aldehydes in ethanol proceeded smoothly to give polysubstituted 1,2,3,4-tetrahydroquinolines in moderate yields. The reaction is believed to involve the Povarov reaction of in situ generated β-enamino ester with the in situ formed aromatic imine.
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spelling pubmed-35110202012-12-03 Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes Sun, Jing Gao, Hong Wu, Qun Yan, Chao-Guo Beilstein J Org Chem Full Research Paper In the presence of p-toluenesulfonic acid as catalyst the domino reaction of arylamines, methyl propiolates and aromatic aldehydes in ethanol proceeded smoothly to give polysubstituted 1,2,3,4-tetrahydroquinolines in moderate yields. The reaction is believed to involve the Povarov reaction of in situ generated β-enamino ester with the in situ formed aromatic imine. Beilstein-Institut 2012-10-26 /pmc/articles/PMC3511020/ /pubmed/23209520 http://dx.doi.org/10.3762/bjoc.8.211 Text en Copyright © 2012, Sun 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
Sun, Jing
Gao, Hong
Wu, Qun
Yan, Chao-Guo
Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes
title Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes
title_full Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes
title_fullStr Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes
title_full_unstemmed Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes
title_short Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes
title_sort facile synthesis of functionalized tetrahydroquinolines via domino povarov reactions of arylamines, methyl propiolate and aromatic aldehydes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3511020/
https://www.ncbi.nlm.nih.gov/pubmed/23209520
http://dx.doi.org/10.3762/bjoc.8.211
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