A mechanistic study of the ammonolysis of alkyl acetoacetates in water. Formation of 1,5-dimethyl-2,6,9- triazabicyclo[3.3.1]nonane-3,7-dione as the main product

R. Paredes, R. Abonia, J. Cadavid, Rodolfo Moreno-Fuquen, A. Jaramillo, A. Hormaza, A. Ramirez, A.R. Kennedy

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Abstract

Ammonolysis of alkyl acetoacetates with 15% NH3 in water at room temperature initially lead to formation of alkyl β-aminocrotonates which slowly converted into 1,5-dimethyl-2,6,9-triaza-bicyclo[3.3.1]nonane-3,7-dione as the main product.
Original languageEnglish
Pages (from-to)55-60
Number of pages5
JournalTetrahedron
Volume58
Issue number1
DOIs
Publication statusPublished - 27 Nov 2001

Keywords

  • Ammonolysis
  • alkyl acetoacetates
  • temperature
  • aminocrotonates

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