| Molecular diversity of triphenylphosphine promoted reaction of electron-deficient alkynes and arylidene Meldrum acid(N,N’-dimethylbarbituric acid) |
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| 引用本文： | Ying Han,Hui Zheng,Yuan-Yuan Zhang,Chao-Guo Yan. Molecular diversity of triphenylphosphine promoted reaction of electron-deficient alkynes and arylidene Meldrum acid(N,N’-dimethylbarbituric acid)[J]. 中国化学快报, 2020, 31(5): 1337-1341. DOI: 10.1016/j.cclet.2019.10.042 |
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| 作者姓名： | Ying Han Hui Zheng Yuan-Yuan Zhang Chao-Guo Yan |
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| 作者单位： | College of Chemistry&Chemical Engineering |
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| 基金项目： | financially supported by the National Natural Science Foundation of China(No.21572196);the Priority Academic Program Development of Jiangsu Higher Education Institutions。 |
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| 摘 要： | The three-component reaction of triphenylphosphine,dimethyl hex-2-en-4-ynedioate and arylidene N,N’-dimethylbarbituric acids in dry methylene dichloride at room temperature afforded trans-1,3-disubstituted 7,9-diazaspiro[4.5]dec-1-enes in good yields and with high diastereoselectivity.However,the similar three-component reaction with arylidene Meldrum acids resulted in a mixtures of cis/trans-1,2-disubstituted 7,9-dioxaspiro[4.5]dec-1-enes.Additionally,the three-component reaction of triphenylphosphine,dimethyl but-2-ynedioate and arylidene Meldrum acids gave polysubstituted 5-(triphe nyl-λ~5-phosphanylidene)cyclopenta-1,3-die nes.A plausible reaction mechanism was proposed for the formation of various products with different regioselectivity and diastereoselectivity.
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| 关 键 词： | PHOSPHINE Electron-deficient alkyne Meldrum acid Barbituric acid Spiro compound |
| 收稿时间： | 2019-09-25 |
Molecular diversity of triphenylphosphine promoted reaction of electron-deficient alkynes and arylidene Meldrum acid (N,N'-dimethylbarbituric acid) |
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| Affiliation: | 1. Institutes of Biomedical Sciences and School of Pharmacy, Fudan University, Shanghai 200433, China;2. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China |
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| Abstract: | The three-component reaction of triphenylphosphine, dimethyl hex-2-en-4-ynedioate and arylidene N,N'-dimethylbarbituric acids in dry methylene dichloride at room temperature afforded trans-1,3-disubstituted 7,9-diazaspiro[4.5]dec-1-enes in good yields and with high diastereoselectivity. However, the similar three-component reaction with arylidene Meldrum acids resulted in a mixtures of cis/trans-1,2-disubstituted 7,9-dioxaspiro[4.5]dec-1-enes. Additionally, the three-component reaction of triphenylphosphine, dimethyl but-2-ynedioate and arylidene Meldrum acids gave polysubstituted 5-(triphenyl-λ5-phosphanylidene)cyclopenta-1,3-dienes. A plausible reaction mechanism was proposed for the formation of various products with different regioselectivity and diastereoselectivity. |
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| Keywords: | Phosphine Electron-deficient alkyne Meldrum acid Barbituric acid Spiro compound |
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