Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels–Alder reactions

Substituted 3,4-dihydro-1,8-naphthyridin-2(1H)-ones have been synthesized with the inverse electron-demand Diels–Alder reaction from 1,2,4-triazines bearing an acylamino group with a terminal alkyne side chain. Alkynes were first subjected to the Sonogashira cross-coupling reaction with aryl halides...

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Autores principales: Fadel, Salah, Hajbi, Youssef, Khouili, Mostafa, Lazar, Said, Suzenet, Franck, Guillaumet, Gérald
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943289/
https://www.ncbi.nlm.nih.gov/pubmed/24605148
http://dx.doi.org/10.3762/bjoc.10.24
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author Fadel, Salah
Hajbi, Youssef
Khouili, Mostafa
Lazar, Said
Suzenet, Franck
Guillaumet, Gérald
author_facet Fadel, Salah
Hajbi, Youssef
Khouili, Mostafa
Lazar, Said
Suzenet, Franck
Guillaumet, Gérald
author_sort Fadel, Salah
collection PubMed
description Substituted 3,4-dihydro-1,8-naphthyridin-2(1H)-ones have been synthesized with the inverse electron-demand Diels–Alder reaction from 1,2,4-triazines bearing an acylamino group with a terminal alkyne side chain. Alkynes were first subjected to the Sonogashira cross-coupling reaction with aryl halides, the product of which then underwent an intramolecular inverse electron-demand Diels–Alder reaction to yield 5-aryl-3,4-dihydro-1,8-naphthyridin-2(1H)-ones by an efficient synthetic route.
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spelling pubmed-39432892014-03-06 Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels–Alder reactions Fadel, Salah Hajbi, Youssef Khouili, Mostafa Lazar, Said Suzenet, Franck Guillaumet, Gérald Beilstein J Org Chem Full Research Paper Substituted 3,4-dihydro-1,8-naphthyridin-2(1H)-ones have been synthesized with the inverse electron-demand Diels–Alder reaction from 1,2,4-triazines bearing an acylamino group with a terminal alkyne side chain. Alkynes were first subjected to the Sonogashira cross-coupling reaction with aryl halides, the product of which then underwent an intramolecular inverse electron-demand Diels–Alder reaction to yield 5-aryl-3,4-dihydro-1,8-naphthyridin-2(1H)-ones by an efficient synthetic route. Beilstein-Institut 2014-01-28 /pmc/articles/PMC3943289/ /pubmed/24605148 http://dx.doi.org/10.3762/bjoc.10.24 Text en Copyright © 2014, Fadel 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
Fadel, Salah
Hajbi, Youssef
Khouili, Mostafa
Lazar, Said
Suzenet, Franck
Guillaumet, Gérald
Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels–Alder reactions
title Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels–Alder reactions
title_full Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels–Alder reactions
title_fullStr Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels–Alder reactions
title_full_unstemmed Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels–Alder reactions
title_short Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels–Alder reactions
title_sort synthesis of 3,4-dihydro-1,8-naphthyridin-2(1h)-ones via microwave-activated inverse electron-demand diels–alder reactions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943289/
https://www.ncbi.nlm.nih.gov/pubmed/24605148
http://dx.doi.org/10.3762/bjoc.10.24
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