Ritter reaction on terpenoids. IV. Remarkable tendency to produce 3-aza-bicyclo[3.3.1]non-2-ene systems from mono and sesquiterpenes

Reaction of cyclic and acyclic monoterpenes with acetonitrile under Ritter type conditions was investigated. An unusual tendency to obtain racemic 8-acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo [3.3.1] non-2-ene perchlorate was observed in all cases regardless of the starting terpene. It is worthy to...

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Detalles Bibliográficos
Autores principales: Rodriguez, J.B., Gros, E.G., Caram, J.A., Marschoff, C.M.
Formato: JOUR
Materias:
3 azabicyclo[3,3,1]nonane derivative
bicyclo[3.3.1]nonane derivative
terpenoid
unclassified drug
article
drug synthesis
methodology
reaction analysis
stereochemistry
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00404039_v36_n43_p7825_Rodriguez
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario:Reaction of cyclic and acyclic monoterpenes with acetonitrile under Ritter type conditions was investigated. An unusual tendency to obtain racemic 8-acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo [3.3.1] non-2-ene perchlorate was observed in all cases regardless of the starting terpene. It is worthy to pointing out that when linear terpenes were used, the reaction is believed to follow a biomimetic pathway forming cyclic cationic species before reacting with the nitrile to form the same byciclic frame. If 3,5-ditrifluoromethylbenzonitrile was employed the corresponding isobornylamide derivative was obtained instead. © 1995 Elsevier Science Ltd.

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