AM1 QUANTUM-CHEMICAL STUDY OF THE MECHANISM OF THE CYCLOCONDENSATION OF 4-HYDROXY-4-METHYL-2-PENTANONE WITH ETHYL CYANOACETATE

Authors

  • М. Флейшер Latvian Institute of Organic Synthesis, LV-1006, Riga
  • Д. Янсоне Latvian Institute of Organic Synthesis, LV-1006, Riga
  • Э. Лукевиц Latvian Institute of Organic Synthesis, LV-1006, Riga

DOI:

https://doi.org/10.1007/7671

Keywords:

lactam, AM1, domino reaction, mechanism, cyclocondensation

Abstract

The reaction of 4-hydroxy-4-methyl-2-pentanone with ethyl cyanoacetate in the presence of ammonium acetate is a consecutive-parallel multistep domino process. The regioselectivity of the reaction is due to the direction of the electrophilic attack of the intermediate formed in the first step,  namely,  ethyl 2-cyano-3,5-dihydroxy-3,5-dimethylhexanoate.

How to Cite
Fleisher, M.; Jansone, D.; Lukevics, E.  Chem. Heterocycl. Compd. 2007, 43, 160. [Khim. Geterotsikl. Soedin. 2007, 209.]

For this article in the English edition see DOI 10.1007/s10593-007-0026-9


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Published

2023-04-03

Issue

No. 2 (2007)

Section

Original Papers