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Synthesis of thia- and thioxo-tetraazaspiro[4.4]nonenones from nitrile imines and arylidenethiohydantoins
Molecular Diversity ( IF 3.8 ) Pub Date : 2020-02-25 , DOI: 10.1007/s11030-020-10056-8 Issa Yavari 1 , Zohreh Taheri 1 , Sara Sheikhi 1 , Samira Bahemmat 2 , Mohammad R Halvagar 2
中文翻译：
从腈亚胺和亚芳基硫代乙内酰脲合成硫杂和硫代四氮杂螺[4.4]壬烯酮
更新日期：2020-02-25
Molecular Diversity ( IF 3.8 ) Pub Date : 2020-02-25 , DOI: 10.1007/s11030-020-10056-8 Issa Yavari 1 , Zohreh Taheri 1 , Sara Sheikhi 1 , Samira Bahemmat 2 , Mohammad R Halvagar 2
Affiliation
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Abstract
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.
Graphic abstract
中文翻译：
从腈亚胺和亚芳基硫代乙内酰脲合成硫杂和硫代四氮杂螺[4.4]壬烯酮
摘要
5-Arylidene-1-methyl-2-thiohydantoins 与腈亚胺发生 [3+2]-环加成反应，在 thiohydantoin 部分的 C=C 和 C=S 偶极亲和体中由腙氯化物原位生成，得到 thioxo-tetraazaspiro[ 4.4]壬烯酮和硫杂-四氮杂螺[4.4]壬烯酮的产量适中。这些螺杂环的立体化学已通过 X 射线衍射研究得到证实。
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