Microwave Assistant Synthesis and Crystal Structures of Two Substituted Oxazole Isoxazole Carboxamides

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摘要 Two novel substituted phenyl oxazole isoxazole carboxamides have been synthesized by microwave assistant technology. The target compounds were characterized by IR, 1H NMR, 13C NMR and HRMS, and their single-crystal structures were further determined by X-ray diffraction. 3-Phenyl-4-(2΄-methyl-2΄- isopropyl-1΄,3΄-oxazole)-5-methyl isoxazole carboxamide (6a) crystallizes in monoclinic system, space group P21/c with a = 6.2137(12), b = 19.923(4), c = 13.748(3) Å, β = 92.30(3)°, V = 1700.6(6) Å3, Dc = 1.228 Mg/m3, Z = 4, F(000) = 672, μ(MoKα) = 0.084 mm-1, R = 0.0526 and wR = 0.1259. 3-(2΄-Fluoro-6΄-chloro-phenyl)-4-(2΄-methyl- 2΄-ethyl-1΄,3΄-oxazole)-5-methyl isoxazole carboxamide (6b) crystallizes in triclinic system, space group P with a = 7.8750(16), b = 10.596(2), c = 11.725(12) Å, β = 102.05(3)°, V = 859.5(3) Å3, Dc = 1.363 Mg/m3, Z = 2, F(000) = 368, μ(MoKα) = 0.250 mm-1, R = 0.0738 and wR = 0.1941. Both of the molecules prefer to form crystal packing through C–H···O hydrogen bonds. Compounds 6a and 6b show safener activity on maize against the injury of chlorsulfuron.

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	康涛
	刘程国
	吴世龙
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	叶非
	付颖

关键词 ： oxazole isoxazole carboxamides, single-crystal structure, synthesis, bioactivity

Abstract：Two novel substituted phenyl oxazole isoxazole carboxamides have been synthesized by microwave assistant technology. The target compounds were characterized by IR, 1H NMR, 13C NMR and HRMS, and their single-crystal structures were further determined by X-ray diffraction. 3-Phenyl-4-(2΄-methyl-2΄- isopropyl-1΄,3΄-oxazole)-5-methyl isoxazole carboxamide (6a) crystallizes in monoclinic system, space group P21/c with a = 6.2137(12), b = 19.923(4), c = 13.748(3) Å, β = 92.30(3)°, V = 1700.6(6) Å3, Dc = 1.228 Mg/m3, Z = 4, F(000) = 672, μ(MoKα) = 0.084 mm-1, R = 0.0526 and wR = 0.1259. 3-(2΄-Fluoro-6΄-chloro-phenyl)-4-(2΄-methyl- 2΄-ethyl-1΄,3΄-oxazole)-5-methyl isoxazole carboxamide (6b) crystallizes in triclinic system, space group P with a = 7.8750(16), b = 10.596(2), c = 11.725(12) Å, β = 102.05(3)°, V = 859.5(3) Å3, Dc = 1.363 Mg/m3, Z = 2, F(000) = 368, μ(MoKα) = 0.250 mm-1, R = 0.0738 and wR = 0.1941. Both of the molecules prefer to form crystal packing through C–H···O hydrogen bonds. Compounds 6a and 6b show safener activity on maize against the injury of chlorsulfuron.

Key words： oxazole isoxazole carboxamides single-crystal structure synthesis bioactivity

收稿日期: 2019-12-12 出版日期: 2020-10-10

基金资助:This work was supported by the National Natural Science Foundation of China (Nos. 31801784 and 31572042), Natural Science Foundation of Heilongjiang Province (No. ZD2017002), and the Research Science Foundation in Technology Innovation of Harbin (No. 2017RAQXJ0172)

通讯作者: fuying@neau.edu.cn E-mail: fuying@neau.edu.cn

引用本文:

康涛;刘程国;吴世龙;高爽;叶非;付颖. Microwave Assistant Synthesis and Crystal Structures of Two Substituted Oxazole Isoxazole Carboxamides[J]. 结构化学, 2020, 39(10): 1906-1911.
KANG Tao;LIU Cheng-Guo;WU Shi-Long;GAO Shuang;YE Fei;FU Ying. Microwave Assistant Synthesis and Crystal Structures of Two Substituted Oxazole Isoxazole Carboxamides. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2020, 39(10): 1906-1911.

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http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2020/V39/I10/1906

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