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

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...

Full description

Bibliographic Details
Main Authors: Salah Fadel, Youssef Hajbi, Mostafa Khouili, Said Lazar, Franck Suzenet, Gérald Guillaumet
Format: Article
Language:English
Published: Beilstein-Institut 2014-01-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
inverse-electron-demand Diels–Alder reaction
microwave irradiation
naphthyridin-2(1H)-ones
Sonogashira cross-coupling
1,2,4-triazine
Online Access:https://doi.org/10.3762/bjoc.10.24
Description
Summary: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.
ISSN:1860-5397

Similar Items