Cyclisation of novel amino oxo esters to tetramic acids - Density functional theory study of the reaction mechanism
Cyclisation of novel amino oxo esters to tetramic acids - Density functional theory study of the reaction mechanism
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.
acylation, cyclization, density functional theory, medicinal chemistry
4593-4600
Detsi, A.
3c021521-4b69-445c-b575-94aca38a85a2
Afantitis, A.
c11398c6-de7d-4acc-9796-bc5c5409d714
Athanasellis, G.
b18842f3-ad1c-455e-aa15-51b1d89b2a57
Markopoulos, J.
0795d115-70c9-4f93-9779-fc2fb0bcbf68
Igglessi-Markopoulou, O.
5ce1a6d8-8446-4797-9416-5c5a550b2ca8
Skylaris, C.K.
8f593d13-3ace-4558-ba08-04e48211af61
19 November 2003
Detsi, A.
3c021521-4b69-445c-b575-94aca38a85a2
Afantitis, A.
c11398c6-de7d-4acc-9796-bc5c5409d714
Athanasellis, G.
b18842f3-ad1c-455e-aa15-51b1d89b2a57
Markopoulos, J.
0795d115-70c9-4f93-9779-fc2fb0bcbf68
Igglessi-Markopoulou, O.
5ce1a6d8-8446-4797-9416-5c5a550b2ca8
Skylaris, C.K.
8f593d13-3ace-4558-ba08-04e48211af61
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), .
(doi:10.1002/ejoc.200300422).
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.
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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
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Date deposited: 31 Jul 2008
Last modified: 16 Mar 2024 03:51
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Contributors
Author:
A. Detsi
Author:
A. Afantitis
Author:
G. Athanasellis
Author:
J. Markopoulos
Author:
O. Igglessi-Markopoulou
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