A Straightforward Approach to
Substituted 2-(Hydroxymethyl)-2,3-dihydrofuro[2,3-b]pyridines and 3-Hydroxy-3,4-dihydro-2H-pyrano[2,3-b]pyridines

Youssef Hajbi; Franck Suzenet; Mostafa Khouili; Said Lazar; Gérald Guillaumet

doi:10.1055/s-0029-1218665

PAPER

A Straightforward Approach to Substituted 2-(Hydroxymethyl)-2,3-dihydrofuro[2,3-b]pyridines and 3-Hydroxy-3,4-dihydro-2H-pyrano[2,3-b]pyridines

Youssef Hajbi^a,b, Franck Suzenet*^a, Mostafa Khouili^b, Said Lazar^c, Gérald Guillaumet*^a
^a Institut de Chimie Organique & Analytique, Université d’Orléans, UMR-CNRS 6005, BP 6759, 45067 Orléans, France
Fax: +33(2)38417281; e-Mail: franck.suzenet@univ-orleans.fr; e-Mail: gerald.guillaumet@univ-orleans.fr;
^b Laboratoire de Chimie Organique & Analytique, Université Sultan Moulay Slimane, BP 523, 23000 Béni Mellal, Morocco
^c Laboratoire de Biochimie, Environnement & Agroalimentaire (URAC 36), Université Hassan II Mohammedia-Casablanca, BP 146, 20800 Mohammedia, Morocco

Abstract

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Abstract

An efficient route to 2-(hydroxymethyl)-2,3-dihydrofuro[2,3-b]pyridines and 3-hydroxy-3,4-dihydro-2H-pyrano[2,3-b]pyridines is reported. The strategy is based on an intramolecular inverse electron demand Diels-Alder reaction starting from 1,2,4-triazines. The hydroxy function comes from the glycidol ring opening with alkynyllithium or alkynylorganoalane.

Key words

alkynes - cycloadditions - Diels-Alder reactions - fused-ring systems - heterocycles

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References

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