Synthesis of novel 3-amino-5-trifluoromethylazoles: A convenient method of obtaining N-(azol-3-yl)amines

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-amino4-etlioxy-1,1,1,-trifluorobut-3-en-2-ones [CF3COCH=C(OEt)NHR, where R=H, Me, Et, CH2CH2OH, CMe2Et, CH2Ph, Ph, 4-NH2C6H4, 4-...

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Published inSynthesis (Stuttgart) no. 9; pp. 1485 - 1493
Main Authors Martins, MAP, Cunico, W, Brondani, S, Peres, RL, Zimmermann, N, Rosa, FA, Fiss, GF, Zanatta, N, Bonacorso, HG
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 03.05.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
azolylation
ETHERS
ACID
amines
isoxazoles
pyrazoles
enones
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Summary: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-amino4-etlioxy-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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-926443