Citation: Han Ying, Zheng Hui, Zhang Yuan-Yuan, Yan Chao-Guo. Molecular diversity of triphenylphosphine promoted reaction of electron-deficient alkynes and arylidene Meldrum acid (N, N'-dimethylbarbituric acid)[J]. Chinese Chemical Letters, ;2020, 31(5): 1337-1341. doi: 10.1016/j.cclet.2019.10.042 shu

Molecular diversity of triphenylphosphine promoted reaction of electron-deficient alkynes and arylidene Meldrum acid (N, N'-dimethylbarbituric acid)

College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China

cgyan@yzu.edu.cn

Received Date: 25 September 2019
Revised Date: 17 October 2019
Available Online: 7 November 2019

Figures(6)

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.
- Phosphine,
- Electron-deficient alkyne,
- Meldrum acid,
- Barbituric acid,
- Spiro compound
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