Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition

A three-component cascade reaction involving 2-alkenyl aniline, aldehydes, and ethyl cyanoacetate in the presence of DBU to synthesize highly substituted 1,2,3,4-tetrahydroquinolines is reported. The reaction proceeded through the Knoevenagel condensation of ethyl cyanoacetate with aldehydes followe...

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Detalles Bibliográficos
Autores principales: Palanimuthu, Arunan, Chen, Chinpiao, Lee, Gene-Hsian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9051536/
https://www.ncbi.nlm.nih.gov/pubmed/35492978
http://dx.doi.org/10.1039/d0ra01264e
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author Palanimuthu, Arunan
Chen, Chinpiao
Lee, Gene-Hsian
author_facet Palanimuthu, Arunan
Chen, Chinpiao
Lee, Gene-Hsian
author_sort Palanimuthu, Arunan
collection PubMed
description A three-component cascade reaction involving 2-alkenyl aniline, aldehydes, and ethyl cyanoacetate in the presence of DBU to synthesize highly substituted 1,2,3,4-tetrahydroquinolines is reported. The reaction proceeded through the Knoevenagel condensation of ethyl cyanoacetate with aldehydes followed by the aza-Michael–Michael addition with 2-alkenyl anilines to prepare the tetrahydroquinoline scaffolds.
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spelling pubmed-90515362022-04-29 Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition Palanimuthu, Arunan Chen, Chinpiao Lee, Gene-Hsian RSC Adv Chemistry A three-component cascade reaction involving 2-alkenyl aniline, aldehydes, and ethyl cyanoacetate in the presence of DBU to synthesize highly substituted 1,2,3,4-tetrahydroquinolines is reported. The reaction proceeded through the Knoevenagel condensation of ethyl cyanoacetate with aldehydes followed by the aza-Michael–Michael addition with 2-alkenyl anilines to prepare the tetrahydroquinoline scaffolds. The Royal Society of Chemistry 2020-04-03 /pmc/articles/PMC9051536/ /pubmed/35492978 http://dx.doi.org/10.1039/d0ra01264e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Palanimuthu, Arunan
Chen, Chinpiao
Lee, Gene-Hsian
Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition
title Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition
title_full Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition
title_fullStr Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition
title_full_unstemmed Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition
title_short Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition
title_sort synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-michael–michael addition
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9051536/
https://www.ncbi.nlm.nih.gov/pubmed/35492978
http://dx.doi.org/10.1039/d0ra01264e
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AT chenchinpiao synthesisofhighlysubstitutedtetrahydroquinolinesusingethylcyanoacetateviaazamichaelmichaeladdition
AT leegenehsian synthesisofhighlysubstitutedtetrahydroquinolinesusingethylcyanoacetateviaazamichaelmichaeladdition

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