Synthesis of 3-Acylpyrroles, 3-(Alkoxycarbonyl) pyrroles, 1, 5, 6, 7-Tetrahydro-4H-indol-4-ones and 3-Benzoylpyridines Based on Staudinger-Aza-Wittig Reactions of 1 …

…, I Hussain, A Riahi, O Fatunsin, C Fischer, P Langer

Index: Bellur, Esen; Yawer, Mirza A.; Hussain, Ibrar; Riahi, Abdolmajid; Fatunsin, Olumide; Fischer, Christine; Langer, Peter Synthesis, 2009 , # 2 p. 227 - 242

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Citation Number: 6

Abstract

Optimal results were obtained when the reaction was carried out using a small excess of 2 (1.2 equiv) and of Ph 3 P (1.3 equiv) (THF, reflux, 8 h). The transformation of 3a into the desired pyrrole 4a required a thorough optimization of the conditions (Table [¹] ). Treatment of a CH 2 Cl 2 solution of 3a, prepared from methyl acetoacetate (1a), with TFA at 0-20 ˚C afforded 4a in 22% yield (method A). The yield was increased to 35% by treatment of 3a in CH 2 Cl 2 with Me 3 ...