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Synthesis and crystal structure of isoxazoline derivatives bearing a 1,2,4-triazole moiety

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Abstract

Novel isoxazoline derivatives bearing a 1,2,4-triazole moiety have been synthesized starting from 2-bromo-1-phenylethanone. Chalcones were obtained by aldol condensation of 1-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanone and 4-substituted benzaldehydes using piperidine as catalyst. Finally, 1,3-dipolar cycloaddition of the chalcones and a variety of aldoximes in the presence of chloramine-T afforded the title compounds. The structural identities of these compounds were confirmed on the basis of IR, NMR, mass spectral, and elemental analysis data and by X-ray analysis of a typical example of the new class of isoxazoline analogs.

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Acknowledgments

We are grateful to the Key SCI-Tech Innovation Team of Zhejiang Province (2010R5 0017) for financial help.

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Authors and Affiliations

  1. College of Material and Chemical Engineering, Hangzhou Normal University, Hangzhou, 310036, Zhejiang, People’s Republic of China

    Zhi-Qiang Dong, Fang-Ming Liu & Sheng-Qin Chen

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  1. Zhi-Qiang Dong
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  2. Fang-Ming Liu
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  3. Sheng-Qin Chen
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Correspondence to Fang-Ming Liu.

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Dong, ZQ., Liu, FM. & Chen, SQ. Synthesis and crystal structure of isoxazoline derivatives bearing a 1,2,4-triazole moiety. Monatsh Chem 143, 1523–1528 (2012). https://doi.org/10.1007/s00706-012-0722-8

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  • DOI: https://doi.org/10.1007/s00706-012-0722-8

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