Synthesis

Synthesis of new dehydro 2-azatryptophans and derivatives via Heck cross-coupling reactions of 3-iodoindazoles with methyl 2-(acetylamino) acrylate

F Crestey, V Collot, S Stiebing, S Rault

Index: Crestey, Francois; Collot, Valerie; Stiebing, Silvia; Rault, Sylvain Synthesis, 2006 , # 20 p. 3506 - 3514

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Citation Number: 17

Abstract

Initially, we attempted to prepare acrylate 1 by the reaction of acetamide with methyl pyruvate in the presence of a catalytic amount of p-toluenesulfonic acid (PTSA) under reflux conditions in toluene (Dean-Stark). The yields were consistently lower than 50%, presumably due to acrylate polymerization; however, addition of 4-methoxyphenol (0.1%) significantly improved the yield and acrylate 1 was then obtained with 61% yield (Scheme [2] ). ... Scheme 2 Reagents ...