Synthese de pyrroles et d'oxazoles par pyrolyse de N-(hydroxy-2′ ethyl) amino-3 propenoate

C Pale-Grosdemange, J Chuche

Index: Pale-Grosdemange, Catherine; Chuche, Josselin Tetrahedron, 1989 , vol. 45, # 11 p. 3397 - 3414

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Citation Number: 8

Abstract

The gas phas pyrolysis of various N-(2′-hydroxyethyl)-3-amino propenoates 1–6 and N- (2′-hydroxy-2′-phenyl ethyl)-3-amino propenoate 7–9 at 390°–420° C leads respectively to formylpyrroles 11–16 and benzoylpyrroles 17–19 and, in some cases, to substituted oxazoles 36–39. The results are best explained by the intermediate formation of dicarbonyl derivative followed either by an intramolecular thermal crotonisation or a six π ...