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Cyclisation of novel amino oxo esters to tetramic acids - Density functional theory study of the reaction mechanism

Record type: Article

The synthesis of novel N-urethane-protected -methylamino--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 -amino--oxo esters to tetramic acids was studied theoretically by the B3LYP hybrid density functional method.

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Citation

Detsi, A., Afantitis, A., Athanasellis, G., Markopoulos, J., Igglessi-Markopoulou, O. and Skylaris, C.K. (2003) Cyclisation of novel amino oxo esters to tetramic acids - Density functional theory study of the reaction mechanism European Journal of Organic Chemistry, (23), pp. 4593-4600. (doi:10.1002/ejoc.200300422).

More information

Published date: 19 November 2003
Keywords: acylation, cyclization, density functional theory, medicinal chemistry

Identifiers

Local EPrints ID: 54167
URI: http://eprints.soton.ac.uk/id/eprint/54167
ISSN: 1434-193X
PURE UUID: addb6a26-5400-43ae-b947-488e8dda5f1e

Catalogue record

Date deposited: 31 Jul 2008
Last modified: 17 Jul 2017 14:36

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Contributors

Author: A. Detsi
Author: A. Afantitis
Author: G. Athanasellis
Author: J. Markopoulos
Author: O. Igglessi-Markopoulou
Author: C.K. Skylaris

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