Efficient synthesis of 2, 3, 4-trisubstituted furans from the reaction of activated acetylenes with ethyl bromopyruvate in the presence of enaminones

I Yavari, Z Hossaini, M Sabbaghan

Index: Yavari, Issa; Hossaini, Zinatossadat; Sabbaghan, Maryam Monatshefte fur Chemie, 2008 , vol. 139, # 8 p. 945 - 948

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Citation Number: 2

Abstract

Abstract The reaction of dialkyl acetylenedicarboxylates or diaroylacetylenes with ethyl bromopyruvate in the presence of enaminones led to 2-ethyl 3, 4-dialkyl 4-bromo-4, 5- dihydro-2, 3, 4-furantricarboxylates or ethyl 3, 4-diaroyl-4-bromo-4, 5-dihydro-2- furancarboxylate in excellent yields. These compounds are quantitatively converted to the corresponding 2, 3, 4-trisubstituted furans by 4-dimethylaminopyridine.