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Paper | Regular issue | Vol 36, No. 7, 1993, pp.1589-1599
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6353
A New Synthetic Route to the Previously Unattainable 3-Substituted 2,3-Dihydro-1,4-dioxino[2,3-b]pyridines

Abdelhakim Benarab, Pascal Poirot, and Gerald Guillaumet*

*Laboratoire de Chimie Bioorganique et Analytique, URA-CNRS N° 499, Université d’Orléans, BP 6759, Rue de Chartres, 45067 Orleans Cedex 2, France

Abstract

A variety of 3-substituted-2,3-dihydro-1,4-dioxino[2,3-b]pyridines (3) have been synthesized from the readily available 2-chloro-3-oxiranylmethoxypyridine (1). Treatment of this epoxide by various nucleophile reagents provided alcohols (2a-i) which, by displacement of the chlorine, gave the desired products (3a-i) in satisfactory yields.