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


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).

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Description/Abstract

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.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1002/ejoc.200300422
ISSNs: 1434-193X (print)
Keywords: acylation, cyclization, density functional theory, medicinal chemistry
Subjects:
ePrint ID: 54167
Date :
Date Event
19 November 2003Published
Date Deposited: 31 Jul 2008
Last Modified: 16 Apr 2017 17:47
Further Information:Google Scholar
URI: http://eprints.soton.ac.uk/id/eprint/54167

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