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Synthesis and Theoretical Study of Mannich Type Reaction Products of 3-Formylchromones with Triazoles and Amides and Nucleophilic Formation of 2,3-Disubstituted-4-Chromanones

The semiempirical PM3 method has been used to study possible reaction paths of the condensation of 3-formylchromones with amides and triazoles. Optimal geometries of intermediates 7, products 8 and all other putative reaction intermediates were obtained. Pertinent transition states, TS I for the dehydratation to carbocation 13, and TS II for amidoalkylation, were located. The semiempirical PM3 method was also used for the calculation of the heats of formation and optimal structures of 4-chromanones 10 and 4-chromones 11. Several compounds of these types have been prepared. Their structures were proved by elemental analysis and 1H-NMR spectra.

  • Content Type Journal Article
  • Pages 223-235
  • Authors
    • Henrieta Stankovicová, Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK-842 15 Bratislava, Slovakia; Tel.: +42 7 796338; Fax: +42 7 729064 (lacova@fns.uniba.sk)
    • Walter M. F. Fabian, Institute of Organic Chemistry, Karl Franzens University, Heinrichstraße 28, A-8010 Graz, Austria;
    • Margita Lácová, Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK-842 15 Bratislava, Slovakia; Tel.: +42 7 796338; Fax: +42 7 729064 (lacova@fns.uniba.sk)
    • Journal Molecules Online
    • Online ISSN 1433-1373
    • Journal Volume Volume 1
    • Journal Issue Volume 1, Number 10

Autoren:   Henrieta Stankovicová, Walter M. F. Fabian, Margita Lácová
Journal:   Molecules Online
Jahrgang:   2004
Erscheinungsdatum:   19.02.2004
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