Multicomponent Reaction for Diastereoselective Synthesis of Spiro[carbazole-3,4′-pyrazoles] and Spiro[carbazole-3,4′-thiazoles]

Posted on 11.06.2021 - 04:43
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 CuSO4 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, CuSO4 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.

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Zhan, Shao-Cong; Fang, Ren-Jie; Sun, Jing; Yan, Chao-Guo (2021): Multicomponent Reaction for Diastereoselective Synthesis of Spiro[carbazole-3,4′-pyrazoles] and Spiro[carbazole-3,4′-thiazoles]. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.1c00538
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