Zhan Shao-Cong, Fang Ren-Jie, Sun Jing, Yan Chao-Guo
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
J Org Chem. 2021 Jul 2;86(13):8726-8741. doi: 10.1021/acs.joc.1c00538. Epub 2021 Jun 10.
In the presence of copper sulfate, the three-component reaction of aromatic aldehydes, ethylindole-3-acetate and 4-arylidene-5-methyl-2-phenylpyrazol-3-ones, in refluxing toluene afforded spiro[carbazole-3,4'-pyrazoles] in good yields with high diastereoselectivity. More importantly, the similar CuSO promoted the four-component reaction of two molecular aromatic aldehydes with ethylindole-3-acetate and 5-methyl-2-phenyl-pyrazol-3-one resulted in 2,4-diarylspiro[carbazole-3,4'-pyrazoles] in satisfactory yields. Additionally, CuSO promoted the four-component reaction of two molecular aromatic aldehydes, ethylindole-3-acetate and 2-phenylthiazol-4-one, in refluxing toluene gave 2,4-diarylspiro[carbazole-3,4'-thiazoles] with diastereomeric ratios in the range of 3:1 to 20:1.
在硫酸铜存在下，芳香醛、吲哚 - 3 - 乙酸乙酯和4 - 芳基亚甲基 - 5 - 甲基 - 2 - 苯基吡唑 - 3 - 酮在回流甲苯中的三组分反应，以良好的产率和高非对映选择性得到螺[咔唑 - 3,4'-吡唑]。更重要的是，类似的硫酸铜促进了两分子芳香醛与吲哚 - 3 - 乙酸乙酯和5 - 甲基 - 2 - 苯基 - 吡唑 - 3 - 酮的四组分反应，以令人满意的产率得到2,4 - 二芳基螺[咔唑 - 3,4'-吡唑]。此外，硫酸铜促进了两分子芳香醛、吲哚 - 3 - 乙酸乙酯和2 - 苯基噻唑 - 4 - 酮在回流甲苯中的四组分反应，得到非对映体比例在3:1至20:1范围内的2,4 - 二芳基螺[咔唑 - 3,4'-噻唑]。
