Efficent Synthesis of 5-(1-Phenyl-3-phenylprop-2-ynyl)-2,2-pentylidene-1,3-dioxane-4,6-dione Derivatives

doi:10.6023/cjoc201903049

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2892-2897.DOI: 10.6023/cjoc201903049 Previous Articles Next Articles

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5-(1-苯基-3-苯基丙基-2-炔基)-2,2-亚戊基-1,3-二噁烷-4,6-二酮衍生物的有效合成

范乃立^a, 许招会^a^*(), 向正兵^b, 肖强^b, 廖传文^b^*()

a 江西师范大学化学化工学院南昌 330027
b 江西省人民医院外科南昌 330006

收稿日期:2019-03-24 修回日期:2019-04-30 发布日期:2019-05-28
通讯作者: 许招会,廖传文 E-mail:gotoxzh@163.com;jxnclcw@163.com
基金资助:
江西省省研究生创新基金(YC2015-B023);江西省教育厅科技攻关(No. GJJ170170)

Efficent Synthesis of 5-(1-Phenyl-3-phenylprop-2-ynyl)-2,2-pentylidene-1,3-dioxane-4,6-dione Derivatives

Fan, Naili^a, Xu, Zhaohui^a^*(), Xiang, Zhengbing^b, Xiao, Qiang^b, Liao, Chuanwen^b^*()

a Department of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330027
b Department of General Surgery, Jiangxi Province People's Hospital, Nanchang 330006

Received:2019-03-24 Revised:2019-04-30 Published:2019-05-28
Contact: Xu, Zhaohui,Liao, Chuanwen E-mail:gotoxzh@163.com;jxnclcw@163.com
Supported by:
Project supported by the Graduate Innovation Foundation of Jiangxi Province(YC2015-B023);the Science and Technology Research Project of Jiangxi Provincial Education Department(No. GJJ170170)

A convenient and efficient approach for the synthesis of 5-(1-phenyl-3-phenylprop-2-ynyl)-2,2-pentylidene-1,3- dioxane-4,6-dione derivatives through a three-component reaction of aldehydes with 2,2-pentylidene-1,3-dioxane-4,6-dione and arylacetylene in the presence of Cu(OAc)₂·H₂O/Cu is described with 12 examples. The reaction tolerates a wide range of aldehydes furnishing the products with good to excellent isolated yields (65%~88%). Additionally, the synthetic protocol has the advantages of wild conditions, simple operation, and excessive copper reused.

Key words: multicomponent reaction, copper acetate/copper, 2,2-pentylidene-1;3-dioxane-4;6-dione, 5-(1-phenyl-3-phe- nylprop-2-ynyl)-2;2-pentylidene-1;3-dioxane-4,6-dione derivatives

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Fan, Naili, Xu, Zhaohui, Xiang, Zhengbing, Xiao, Qiang, Liao, Chuanwen. Efficent Synthesis of 5-(1-Phenyl-3-phenylprop-2-ynyl)-2,2-pentylidene-1,3-dioxane-4,6-dione Derivatives[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2892-2897.

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Fig. & Tab. 5

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Entry	R	Ar	Time/h	Product	Yield^b/%
1	C₆H₅	C₆H₅	10.0	4a	83
2	4-FC₆H₄	C₆H₅	8.0	4b	69
3	4-ClC₆H₄	C₆H₅	8.0	4c	70
4	4-CH₃C₆H₄	C₆H₅	6.0	4d	75
5	4-NO₂C₆H₄	C₆H₅	12.0	4e	71
6	4-CH₃OC₆H₄	C₆H₅	8.0	4f	66
7	2-Furyl	C₆H₅	6.0	4g	85
8	PhCH=CH	C₆H₅	12.0	4h	88
9	CH₃	C₆H₅	20.0	4i	60
10	CH₃CH₂CH₂	C₆H₅	20.0	4j	63
11	C₆H₅	4-ClC₆H₄	8.0	4k	76
12	CH₃CH₂CH₂	4-ClC₆H₄	20.0	4l	70

Entry	R	Ar	Time/h	Product	Yield^b/%
1	C₆H₅	C₆H₅	10.0	4a	83
2	4-FC₆H₄	C₆H₅	8.0	4b	69
3	4-ClC₆H₄	C₆H₅	8.0	4c	70
4	4-CH₃C₆H₄	C₆H₅	6.0	4d	75
5	4-NO₂C₆H₄	C₆H₅	12.0	4e	71
6	4-CH₃OC₆H₄	C₆H₅	8.0	4f	66
7	2-Furyl	C₆H₅	6.0	4g	85
8	PhCH=CH	C₆H₅	12.0	4h	88
9	CH₃	C₆H₅	20.0	4i	60
10	CH₃CH₂CH₂	C₆H₅	20.0	4j	63
11	C₆H₅	4-ClC₆H₄	8.0	4k	76
12	CH₃CH₂CH₂	4-ClC₆H₄	20.0	4l	70

5-(1-苯基-3-苯基丙基-2-炔基)-2,2-亚戊基-1,3-二噁烷-4,6-二酮衍生物的有效合成

Efficent Synthesis of 5-(1-Phenyl-3-phenylprop-2-ynyl)-2,2-pentylidene-1,3-dioxane-4,6-dione Derivatives

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Entry	Copper salt	Reductant	Time/h	Yield^b/%
1	CuSO₄?5H₂O	Cu	24	51
2	CuCl₂?2H₂O	Cu	24	39
3	Cu₂(CO₃)(OH)₂	Cu	24	12
4	Cu(acac)₂	Cu	24	44
5	Cu(NH₃)₄SO₄	Cu	24	31
6^c	CuI	—	20	0
7^d	CuOAc	—	10	56
8	Cu(OAc)₂?H₂O	Cu	10	83
9^c		Cu	24	0
10	Cu(OAc)₂?H₂O	Sodium ascorbate	6	75
11^c	Cu(OAc)₂?H₂O	NH₂OH?HCl	6	0
12	Cu(OAc)₂?H₂O	Na₂SO₃	6	53
13	Cu(OAc)₂?H₂O	Cu	8	71
14	Cu(OAc)₂?H₂O	Cu	12	83
15^e	Cu(OAc)₂?H₂O	Cu (recycled)	10	76

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