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Synthesis 2006(9): 1485-1493  
DOI: 10.1055/s-2006-926443
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel 3-Amino-5-trifluoromethylazoles: A Convenient Method of Obtaining N-(Azol-3-yl)amines

Marcos A. P. Martins*, Wilson Cunico, Sergio Brondani, Rodrigo L. Peres, Nilo Zimmermann, Fernanda A. Rosa, Gabriela F. Fiss, Nilo Zanatta, Helio G. Bonacorso
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil
Fax: +55(55)32208756; e-Mail: mmartins@base.ufsm.br;
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Publication History

Received 23 September 2005
Publication Date:
11 April 2006 (online)

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Abstract

A convenient method to obtain 10 3-amino-5-trifluoromethyl-5-hydroxy-4,5-dihydroisoxazoles and 18 3-amino-5-trifluoromethyl-1H-pyrazoles by cyclocondensation reaction of 4-amino-4-ethoxy-1,1,1,-trifluorobut-3-en-2-ones [CF3COCH=C(OEt)NHR, where R = H, Me, Et, CH2CH2OH, CMe2Et, CH2Ph, Ph, 4-NH2C6H4, 4-AcC6H4, 4-NO2C6H4, 5-methylisoxazol-3-yl, thiazol-2-yl, CH2CO2Et, CH(Ph)CO2Me, CH(i-Bu)CO2Et] with hydroxyl­amine, hydrazine and phenylhydrazine is reported.

Key words

isoxazoles - pyrazoles - enones - amines - azolylation

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