Metal-Free Decarboxylative Hetero-Diels–Alder Synthesis of 3-Hydroxypyridines: A Rapid Access to N-Fused Bicyclic Hydroxypiperidine Scaffolds

…, V Tognetti, L Joubert, C Sabot…

Index: Jouanno, Laurie-Anne; Tognetti, Vincent; Joubert, Laurent; Sabot, Cyrille; Renard, Pierre-Yves Organic Letters, 2013 , vol. 15, # 10 p. 2530 - 2533

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Citation Number: 17

Abstract

A complete experimental and theoretical study of the thermally controlled metal-free decarboxylative hetero-Diels–Alder (HDA) reaction of 5-alkoxyoxazoles with acrylic acid is reported. This strategy offers a new entry to valuable 2, 6-difunctionalized 3- hydroxypyridines from readily available 2-and 4-disubstituted 5-alkoxyoxazoles. The reaction conditions proved compatible with, among others, ketone, amide, ester, ether, ...