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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

Paredes, R. and Abonia, R. and Cadavid, J. and Moreno-Fuquen, Rodolfo and Jaramillo, A. and Hormaza, A. and Ramirez, A. and Kennedy, A.R. (2001) 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. Tetrahedron, 58 (1). pp. 55-60. ISSN 0040-4020

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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.