从腈亚胺和苯亚甲基硫代海因出发合成噻和硫代四氮杂螺[4.4]壬-4-烯酮。
Synthesis of thia- and thioxo-tetraazaspiro[4.4]nonenones from nitrile imines and arylidenethiohydantoins.
机构信息
Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran.
Department of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran.
出版信息
Mol Divers. 2021 May;25(2):777-785. doi: 10.1007/s11030-020-10056-8. Epub 2020 Feb 25.
5-Arylidene-1-methyl-2-thiohydantoins undergo [3+2]-cycloaddition reaction with nitrile imines, generated in situ from hydrazonyl chlorides, at C=C and C=S dipolarophiles in the thiohydantoin moiety to afford thioxo-tetraazaspiro[4.4]nonenones and thia-tetraazaspiro[4.4]nonenones in moderate to good yields. The stereochemistry of these spiroheterocycles has been confirmed by X-ray diffraction studies.
5-芳亚甲基-1-甲基-2-硫代海因与腈亚胺发生[3+2]环加成反应，腈亚胺由氯代肼酰基原位生成，在硫代海因部分的 C=C 和 C=S 二亲核体上反应，得到硫代-四氮杂螺[4.4]壬-5-酮和硫杂-四氮杂螺[4.4]壬-5-酮，产率中等至良好。这些螺杂环化合物的立体化学结构已通过 X 射线衍射研究得到证实。
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