Cyclisation of novel amino oxo esters to tetramic acids− density functional theory study of the reaction mechanism

…, O Igglessi??Markopoulou, CK Skylaris

Index: Detsi, Anastasia; Afantitis, Antreas; Athanasellis, Giorgos; Markopoulos, John; Igglessi-Markopoulou, Olga; Skylaris, Chris-Kriton European Journal of Organic Chemistry, 2003 , # 23 p. 4593 - 4600

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Citation Number: 6

Abstract

Abstract The synthesis of novel N-urethane-protected γ-methylamino-β-oxo esters and their use as precursors for the preparation of N-methyltetramic acids is described. The presence of the bulky urethane protecting group on the nitrogen atom gives rise to rotational isomers detectable in the NMR spectra of the compounds, along with the keto/enol tautomerism. The mechanism of the cyclisation reaction of γ-amino-β-oxo esters to tetramic acids was ...