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Synthesis 2010(8): 1349-1355  
DOI: 10.1055/s-0029-1218665
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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 Hajbia,b, Franck Suzenet*a, Mostafa Khouilib, Said Lazarc, 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
Further Information

Publication History

Received 22 October 2009
Publication Date:
05 February 2010 (online)

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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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7

It should be noted that the cycloaddition reaction for the synthesis of the furopyridines was achievable under open-vessel conditions and reaction times were longer (12 h at 180 ˚C). We recently reported that sealed-tube microwave activation dramatically shortened the reaction times (45 min).³a