Synthesis, Structure, and Cyclocondensation of the 4,4,4-Trifluoro-3,3-dihydroxy-2-methyl-1-(thien-2-yl)-1-butanone with Hydroxylamine and Hydrazine

Author:

Flores Alex F. C.1ORCID,Kuhn Bruna P.2,Flores Darlene C.1,Pereira Mariano A.3,Balliano Tatiane L.3,da Silva Givanildo S.3

Affiliation:

1. Escola de Química e Alimentos, Universidade Federal de Rio Grande, 96203-900 Rio Grande, RS, Brazil

2. Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil

3. LabCriMM Instituto de Química e Biotecnologia, Universidade Federal de Alagoas, 57072-970 Maceió, AL, Brazil

Abstract

The synthesis of 4,4,4-trifluoro-3,3-dihydroxy-2-methyl-1-(thien-2-yl)butan-1-one (3) through acylation of 1,1-dimethoxy-1-(thien-2-yl)propane (1) with trifluoroacetic anhydride and its reactions with hydroxylamine and hydrazine was investigated. X-ray structural analysis of new trifluoromethyl-substituted dielectrophile 3 revealed that this hydrate exists as a racemate with inter- and intramolecular O-H·O bonds. The crystal structure shows alignment along axis b of pair molecules with the same configuration of the O2-H·O1 bond. For 5(3)-trifluoromethyl-4-methyl-3(5)-(thien-2-yl)-1H-pyrazole (4), obtained via cyclocondensation of precursor 2 and hydrazine hydrochloride, X-ray structural analysis indicated that its rings are almost planar (torsion angle N2-C5-C6-C7–5.4°) and that S1 at the thienyl moiety is anti-periplanar to N2 (torsion angle N2-C5-C6-S1 176.01); no disorder effect was observed for the thienyl ring.

Funder

Fundação de Amparo à pesquisa do Estado do Rio Grande do Sul

Publisher

Hindawi Limited

Subject

Spectroscopy,Atomic and Molecular Physics, and Optics,Analytical Chemistry

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