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Paper | Regular issue | Vol 29, No. 12, 1989, pp.2369-2377
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5172
New Applications of Westphal Condensation. Synthesis of New [2.3.3]Cyclazinones

Joaquin Pastor, M. Paz Matia, Jose L. García Navío, Juan J. Vaquero, and Jullio Alvarez-Builla*

*Departamento de Química Orgánica, Universidad de Alcalá de Henares, 28871 Alcalá de Henares (Madrid), Spain


Two different types of [2.3.3]cyclazinone isomers were obtained by methods based on the Westphal condensation. 2,6-Dialkylpyridinium salts were condensed with 1,2-acenaphtenequinone to produce [2.3.3]cyclazin-1-one derivatives. By a similar process, a quinolizinium-1-olate was prepared, which was cyclized with DMAD yielding a [2.3.3]cyclazin-6-one derivative.