Synthesis of new azocine derivatives and their functionalization by nucleophilic addition to their iminium salts.

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dc.contributor.authorTrindade, Angela Cristina Leal Badaró
dc.contributor.authorSantos, Daniela Cristina dos
dc.contributor.authorGil, Laurent Frédéric
dc.contributor.authorMarazano, Christian
dc.contributor.authorGil, Rossimiriam Pereira de Freitas
dc.date.accessioned2017-06-07T14:33:00Z
dc.date.available2017-06-07T14:33:00Z
dc.date.issued2005
dc.description.abstractA route to the eight-membered nitrogen heterocycles 20a,b is described starting from the 3-alkyl-N-benzylpyridinium salts 14a,b. These azocine derivatives were converted into their respective iminium salts 11 by treatment with methanesulfonic acid. A study concerning the regioselectivity of nucleophilic additions to these salts is presented. Nucleophiles like Introduction Azocine derivatives are an important and diverse class of compounds that are found in a range of natural and nonnatural products. These eight-membered nitrogen heterocycles are present in complex structures of many natural substances such apparicine (1),[1] magallanesine (2),[2] and manzamine A (3),[3] an important antitumoral marine alkaloid (Figure 1). Among the nonnatural products, the more commonly found azocines are substituted and fully or partly reduced. These compounds have found application as therapeutic agents in view of their various biological properties, for example as antimalarials, antitussives, nasal decongestants, antihypertensives, and analgesics.[4] Another large and much-studied class of compounds containing the azocine ring is synthetic benzofuroazocines (4), which, due their structure close to that of hypnoanalgesics, possess important activity in the central nervous system (CNS).[5] Finally, these monocyclic medium rings have also found use as synthetic intermediates, for example, in the synthesis of the pyrrolizidine ring system,[6] and they constitute important medium-size cycles in conformational studies. [a] Departamento de Química, ICEx, UFMG Av. Antônio Carlos, 6627, Belo Horizonte, MG, Brazil Fax: +55-031-3499-5700 E-mail: rossi@ciclope.lcc.ufmg.br [b] Departamento de Farmácia, SCS, UFPR, Av. Pref. Lothário Meissner, 3400, Jd. Botânico, Curitiba, PR, Brazil [c] Departamento de Química, ICEB, UFOP, Campus Morro do Cruzeiro, Ouro Preto, MG, Brazil [d] Institut de Chimie des Substances Naturelles, Avenue de la Terrasse, 91198, Gif-sur-Yvette, France © 2005 Wiley-VCH Verlag GmbH & Co. 1052 KGaA, Weinheim DOI: 10.1002/ejoc.200400728 Eur. J. Org. Chem. 2005, 1052–1057 hydride or Grignard reagents react selectively in the 2-position to give adducts such as 22 and 23, while azide and phenylthiolate attack the 6-position to give 24 and 25, respectively.pt_BR
dc.identifier.citationTRINDADE, A. C. L. B. et al. Synthesis of new azocine derivatives and their functionalization by nucleophilic addition to their iminium salts. European Journal of Organic Chemistry, v. 6, p. 1052-1057, 2005. Disponível em: <http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200400728/full>. Acesso em: 20 mai. 2017.pt_BR
dc.identifier.doihttps://doi.org/10.1002/ejoc.200400728
dc.identifier.issn1099-0690
dc.identifier.urihttp://www.repositorio.ufop.br/handle/123456789/7901
dc.identifier.uri2http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200400728/fullpt_BR
dc.language.isoen_USpt_BR
dc.rightsrestritopt_BR
dc.subjectAzocinespt_BR
dc.subjectNitrogen heterocyclespt_BR
dc.subjectCycloadditionpt_BR
dc.subjectNucleophilic additionpt_BR
dc.titleSynthesis of new azocine derivatives and their functionalization by nucleophilic addition to their iminium salts.pt_BR
dc.typeArtigo publicado em periodicopt_BR
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