RESEARCH ARTICLE

 

Expedient access to an N-phenylpyrrolidin-2-yl heterocycle via a base-induced intramolecular aza-Michael reaction

 

 

Josierika A. Ferreira Ramos; Tanus J. Nagem; Jason G. Taylor^*

Departamento de Química, ICEB, Universidade Federal de Ouro Preto, Campus Universitário Morro do Cruzeiro, 35400-000, Ouro Preto-MG, Brazil

 

 

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ABSTRACT

Ethyl 2-(1-phenylpiperidin-2-yl) acetate was formed in a spontaneous cyclization from (E)-ethyl 7-oxohept-2-enoate whereas ethyl [1-(2-bromophenyl)-2-pyrrolidinyl] acetate could be synthesized in good overall yield when employing a stoichiometric amount of base to facilitate the intramolecular aza-Michael reaction.

Keywords: aza Michael, intramolecular, catalysed, piperidine, pyrrolidine, base

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Full text available only in pdf format.

 

Acknowledgements

The authors thank the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), the Fundação Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), and the Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG) for financial support. Thanks go to Dr. Robson J. de Cássia Franco Afonso, and Dr Maurício Xavier Coutrim for providing excellent Mass Spectrometry service.

 

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Received 7 October 2011
Revised 31 October 2011
Accepted 23 November 2011

 

 

* To whom correspondence should be addressed. E-mail: jason@iceb.ufop.br