Synthesis of Spirobarbiturate Piperidin-2-one Derivatives via Cascade Aza-Michael/Michael Cyclization Reaction

doi:10.6023/cjoc202105045

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4450-4458.DOI: 10.6023/cjoc202105045 Previous Articles Next Articles

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利用aza-Michael/Michael串联环化反应合成螺巴比妥哌啶酮衍生物

刘雪华^a, 王川川^b, 王新璐^a, 马志伟^b, 孟蕾^c, 丁德刚^b, 刘俊桃^b, 陈亚静^a^,^*()

a 郑州大学药学院郑州 450001
b 河南牧业经济学院理学部郑州 450046
c 河南省兽药饲料监察所郑州 450008

收稿日期:2021-05-26 修回日期:2021-07-02 发布日期:2021-07-23
通讯作者: 陈亚静
作者简介:
† 共同第一作者.
基金资助:
河南省重点研发与推广专项(科技攻关)(202102110067); 河南省重点研发与推广专项(科技攻关)(212102110439); 河南省自然科学基金(202300410188); 河南省自然科学基金(212300410152); 河南牧业经济学院(2019HNUAHEDF011); 河南牧业经济学院(XKYCXJJ2020006)

Synthesis of Spirobarbiturate Piperidin-2-one Derivatives via Cascade Aza-Michael/Michael Cyclization Reaction

Xuehua Liu^a, Chuanchuan Wang^b, Xinlu Wang^a, Zhiwei Ma^b, Lei Meng^c, Degang Ding^b, Juntao Liu^b, Yajing Chen^a()

a School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001
b Faculty of Science, Henan University of Animal Husbandry and Economy, Zhengzhou 450046
c Henan Institute of Veterinary Drug and Feed Control, Zhengzhou 450008

Received:2021-05-26 Revised:2021-07-02 Published:2021-07-23
Contact: Yajing Chen
About author:
† These authors contributed equally to this work.
Supported by:
Key Scientific and Technological Project of Henan Province(202102110067); Key Scientific and Technological Project of Henan Province(212102110439); Natural Science Foundation of Henan Province(202300410188); Natural Science Foundation of Henan Province(212300410152); Henan University of Animal Husbandry and Economy(2019HNUAHEDF011); Henan University of Animal Husbandry and Economy(XKYCXJJ2020006)

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Abstract

A highly efficient cascade aza-Michael/intramolecular-Michael reaction employing barbiturate-derived alkenes and N-alkoxy acrylamides has been developed. The reaction proceeds smoothly under mild conditions and is amenable to gram scale synthesis, providing a practical tool in the synthesis of bioactive spirobarbiturate piperidin-2-ones molecules in moderate to good yields.

Key words: spirobarbiturate, piperidin-2-one, cascade reaction, Michael addition

Cite this article

Xuehua Liu, Chuanchuan Wang, Xinlu Wang, Zhiwei Ma, Lei Meng, Degang Ding, Juntao Liu, Yajing Chen. Synthesis of Spirobarbiturate Piperidin-2-one Derivatives via Cascade Aza-Michael/Michael Cyclization Reaction[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4450-4458.

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Fig. & Tab. 6

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Entry	Base	1a/2a/Base	Solvent	Temp./℃	Yield^b/%
1	K₂CO₃	1.0/1.2/1.2	CH₂Cl₂	25	58
2	Na₂CO₃	1.0/1.2/1.2	CH₂Cl₂	25	54
3	Cs₂CO₃	1.0/1.2/1.2	CH₂Cl₂	25	13
4	K₂HPO₄	1.0/1.2/1.2	CH₂Cl₂	25	Trace
5	K₂CO₃	1.0/1.2/1.2	CH₃CN	25	69
6	K₂CO₃	1.0/1.2/1.2	CHCl₃	25	67
7	K₂CO₃	1.0/1.2/1.2	Toluene	25	21
8	K₂CO₃	1.0/1.2/1.2	DCE	25	29
9	K₂CO₃	1.0/1.2/1.2	THF	25	33
10	K₂CO₃	1.0/1.5/1.2	CH₃CN	25	74
11	K₂CO₃	1.0/2.0/1.2	CH₃CN	25	74
12	K₂CO₃	1.0/1.5/1.5	CH₃CN	25	83
13^c	K₂CO₃	1.0/1.5/1.5	CH₃CN	25	52
14	K₂CO₃	1.0/1.5/1.5	CH₃CN	40	83

Entry	Base	1a/2a/Base	Solvent	Temp./℃	Yield^b/%
1	K₂CO₃	1.0/1.2/1.2	CH₂Cl₂	25	58
2	Na₂CO₃	1.0/1.2/1.2	CH₂Cl₂	25	54
3	Cs₂CO₃	1.0/1.2/1.2	CH₂Cl₂	25	13
4	K₂HPO₄	1.0/1.2/1.2	CH₂Cl₂	25	Trace
5	K₂CO₃	1.0/1.2/1.2	CH₃CN	25	69
6	K₂CO₃	1.0/1.2/1.2	CHCl₃	25	67
7	K₂CO₃	1.0/1.2/1.2	Toluene	25	21
8	K₂CO₃	1.0/1.2/1.2	DCE	25	29
9	K₂CO₃	1.0/1.2/1.2	THF	25	33
10	K₂CO₃	1.0/1.5/1.2	CH₃CN	25	74
11	K₂CO₃	1.0/2.0/1.2	CH₃CN	25	74
12	K₂CO₃	1.0/1.5/1.5	CH₃CN	25	83
13^c	K₂CO₃	1.0/1.5/1.5	CH₃CN	25	52
14	K₂CO₃	1.0/1.5/1.5	CH₃CN	40	83

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利用aza-Michael/Michael串联环化反应合成螺巴比妥哌啶酮衍生物

Synthesis of Spirobarbiturate Piperidin-2-one Derivatives via Cascade Aza-Michael/Michael Cyclization Reaction

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