1. Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives.
- Author
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Jian Wu, Qing Shi, Zhuo Chen, Ming He, Linhong Jin, and Deyu Hu
- Subjects
- *
HETEROCYCLIC compounds synthesis , *PYRAZOLES , *THIOUREA , *CHEMICAL derivatives , *METHYL hydrazine , *RING formation (Chemistry) , *FORMYLATION - Abstract
Sixteen novel pyrazole acyl thiourea derivatives 6 were synthesized from monomethylhydrazine (phenylhydrazine) and ethyl acetoacetate. The key 5-chloro-3- methyl-1-substituted-1H-pyrazole-4-carbonyl chloride intermediates 4 were first generated in four steps through cyclization, formylation, oxidation and acylation. Thess were then reacted with ammonium thiocyanate in the presence of PEG-400 to afford 5-chloro-3- methyl-1-substituted-1H-pyrazole-4-carbonyl isothiocyanates 5. Subsequent reaction with fluorinated aromatic amines resulted in the formation of the title compounds. The synthesized compound were unequivocally characterized by IR, 1H-NMR, 13C-NMR and elemental analysis and some of the synthesized compounds displayed good antifungal activities against Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica and anti-TMV activity in preliminary antifungal activity tests. [ABSTRACT FROM AUTHOR]
- Published
- 2012
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