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Synthesis 2002(16): 2404-2408
DOI: 10.1055/s-2002-35217
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of a New Series of 3-Alkoxy-5-hydroxy-5-trifluoromethylpyrrolidin-2-ones from 1,1,1-Trifluoro-4-alkoxyalk-3-en-2-ones

Nilo Zanatta*, Luciana S. Rosa, Maria F. M. Cortelini, Simone Beux, Ana P. D. Santos, Helio 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 28 September 2001
Publication Date:
04 November 2002 (online)

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Abstract

The synthesis of a new series of 3-alkoxy-5-hydroxy-5-trifluoromethyl pyrrolidin-2-ones 2a-h from the reaction of 1,1,1-trifluoro-4-alkoxyalk-3-en-2-ones 1a-h of the general formula F3CC(O)C(R2)=C(R1)OR, where: R = Me, Et, -(CH2)2-, -(CH2)3-; R1 = H, Me, Ph, p-Me-Ph, p-F-Ph; and R2 = H, Me, -(CH2)2-, -(CH2)3- with sodium cyanide in hydro-alcoholic medium is reported.

Key words

ketones - pyrrolidin-2-ones - lactams - heterocycles - fluorine­