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Synthesis 2010(14): 2348-2354  
DOI: 10.1055/s-0029-1218779
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Synthesis of Oxa- and Aza-Condensed Tetrahydropyridines from Cyclic Enones

Nilo Zanatta*, Liana S. da Fernandes, Sinara München, Helena S. Coelho, Simone S. Amaral, Leonardo Fantinel, Hélio G. Bonacorso, Marcos A. P. Martins
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97.105-900, Santa Maria, RS, Brazil
Fax: +55(55)2208031; e-Mail: zanatta@base.ufsm.br;
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Publication History

Received 18 January 2010
Publication Date:
05 May 2010 (online)

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Abstract

A simple and efficient one-pot synthesis of tetrahydrooxazolo[3,2-a]pyridines and hexahydroimidazo[1,2-a]pyridines, and some related oxa- and aza-condensed tetrahydropyridines, from the reaction of 2-alkoxy-5-(trifluoroacetyl)-2,3-dihydro-2H-pyrans (cyclic enones) with amino alcohols and primary diamines, is reported. Products were isolated with high purity and in very good yields.

Key words

tetrahydropyridines - oxazolopyridines - imidazopyridines - dihydropyrans - cyclic enones

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Crystallographic data for compound 5f (CCDC 754832) can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.