Synthesis of 1-[5-(α-Naphthyl)-2H-Tetrazol-2-Acetyl]-4-Aroylthiosemicarbazides and 3-[5-(α-Naphthyl)-2H-Tetrazol-2-Methylene]-4-Aroyl-1, 2,4-Triazoline-5-Thione Derivatives

Abstract

Abstract: A series of new 1-[5-(α-naphthyl)-2H-tetrazol-2-acetyl]-4-aroylthiosemicarbazides(Ⅱ) weresynthesized by condensation of aroylisothiocyanate with 5-(α-naphthyl-2H-tetrazol-2-acetylhydrazine(Ⅰ) in absolute acetonitrile. Some of 3-[5-(α-naphthyl)-2H-tetrazol-2-methylene]-4-aroyl-1,2,4-triazoline-5-thione(Ⅲ) were prepared by the cyclization of compounds(Ⅱ) under the catalysis of 1 mol/L K₂CO₃solution. The structures of all compounds prepared were characterized by elemental analysis, IR and ¹HNMR. The regioselectivity of the cyclization of compounds (Ⅱ) was rationalized with the fragments of mass spectra of compounds (Ⅲ).Preliminary pharmacological examinations show that the new compounds (Ⅱ) and (Ⅲ) possess some promoting, or inhibiting activity on growth of plumule of wheat.

Key words: Acylthiosemicarbazides, Tetrazole, Heterocyclic 1,2,4-triazoline-5-thione, Biological activity

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Feng Xiao-ming, Chen Rong, Zhang Zi-yi. Synthesis of 1-[5-(α-Naphthyl)-2H-Tetrazol-2-Acetyl]-4-Aroylthiosemicarbazides and 3-[5-(α-Naphthyl)-2H-Tetrazol-2-Methylene]-4-Aroyl-1, 2,4-Triazoline-5-Thione Derivatives[J]. Chem. J. Chinese Universities, 1991, 12(10): 1326.

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Synthesis of 1-[5-(α-Naphthyl)-2H-Tetrazol-2-Acetyl]-4-Aroylthiosemicarbazides and 3-[5-(α-Naphthyl)-2H-Tetrazol-2-Methylene]-4-Aroyl-1, 2,4-Triazoline-5-Thione Derivatives

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