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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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
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_00404039_v36_n43_p7825_Rodriguez2023-10-03T14:50:51Z Ritter reaction on terpenoids. IV. Remarkable tendency to produce 3-aza-bicyclo[3.3.1]non-2-ene systems from mono and sesquiterpenes Rodriguez, J.B. Gros, E.G. Caram, J.A. Marschoff, C.M. 3 azabicyclo[3,3,1]nonane derivative bicyclo[3.3.1]nonane derivative terpenoid unclassified drug article drug synthesis methodology reaction analysis stereochemistry 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. Fil:Rodriguez, J.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Gros, E.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Caram, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Marschoff, C.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00404039_v36_n43_p7825_Rodriguez
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic 3 azabicyclo[3,3,1]nonane derivative
bicyclo[3.3.1]nonane derivative
terpenoid
unclassified drug
article
drug synthesis
methodology
reaction analysis
stereochemistry
spellingShingle 3 azabicyclo[3,3,1]nonane derivative
bicyclo[3.3.1]nonane derivative
terpenoid
unclassified drug
article
drug synthesis
methodology
reaction analysis
stereochemistry
Rodriguez, J.B.
Gros, E.G.
Caram, J.A.
Marschoff, C.M.
Ritter reaction on terpenoids. IV. Remarkable tendency to produce 3-aza-bicyclo[3.3.1]non-2-ene systems from mono and sesquiterpenes
topic_facet 3 azabicyclo[3,3,1]nonane derivative
bicyclo[3.3.1]nonane derivative
terpenoid
unclassified drug
article
drug synthesis
methodology
reaction analysis
stereochemistry
description 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.
format JOUR
author Rodriguez, J.B.
Gros, E.G.
Caram, J.A.
Marschoff, C.M.
author_facet Rodriguez, J.B.
Gros, E.G.
Caram, J.A.
Marschoff, C.M.
author_sort Rodriguez, J.B.
title Ritter reaction on terpenoids. IV. Remarkable tendency to produce 3-aza-bicyclo[3.3.1]non-2-ene systems from mono and sesquiterpenes
title_short Ritter reaction on terpenoids. IV. Remarkable tendency to produce 3-aza-bicyclo[3.3.1]non-2-ene systems from mono and sesquiterpenes
title_full Ritter reaction on terpenoids. IV. Remarkable tendency to produce 3-aza-bicyclo[3.3.1]non-2-ene systems from mono and sesquiterpenes
title_fullStr Ritter reaction on terpenoids. IV. Remarkable tendency to produce 3-aza-bicyclo[3.3.1]non-2-ene systems from mono and sesquiterpenes
title_full_unstemmed Ritter reaction on terpenoids. IV. Remarkable tendency to produce 3-aza-bicyclo[3.3.1]non-2-ene systems from mono and sesquiterpenes
title_sort ritter reaction on terpenoids. iv. remarkable tendency to produce 3-aza-bicyclo[3.3.1]non-2-ene systems from mono and sesquiterpenes
url http://hdl.handle.net/20.500.12110/paper_00404039_v36_n43_p7825_Rodriguez
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