Efficient Copper-Catalyzed Domino Synthesis of Phosphonated Isoquinolin-1(2H)-ones Using Cyanomethylphosphonates as Building Blocks

doi:10.6023/cjoc202008045

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 258-266.DOI: 10.6023/cjoc202008045 Previous Articles Next Articles

Article

以氰甲基亚磷酸酯为含膦试剂的铜催化膦酰化异喹啉酮类化合物的高效合成

赵苏艳^a^,^b, 宫雪芹^c, 甘子玉^c, 颜秋莉^b, 刘学良^d^,^*(), 杨道山^b^,^c^,^*()

a 吉林警察学院实验技术中心长春 130117
b 青岛科技大学化学与分子工程学院山东青岛 266042
c 曲阜师范大学化学与化工学院山东曲阜 273165
d 新乡医学院基础医学院河南新乡 453003

收稿日期:2020-08-25 修回日期:2020-10-18 发布日期:2020-10-22
通讯作者: 刘学良, 杨道山
作者简介:
* Corresponding authors. E-mail: liuxueliang@xxmu.edu.cn; yangdaoshan@tsinghua.org.cn
基金资助:
山东省自然科学基金(ZR2016JL012); 青岛科技大学高科技人才资助项目.

Efficient Copper-Catalyzed Domino Synthesis of Phosphonated Isoquinolin-1(2H)-ones Using Cyanomethylphosphonates as Building Blocks

Suyan Zhao^a^,^b, Xueqin Gong^c, Ziyu Gan^c, Qiuli Yan^b, Xueliang Liu^d^,^*(), Daoshan Yang^b^,^c^,^*()

a Experimental Technology Center, Jilin Police College, Changchun 130117
b College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042
c School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165
d Basic Medical College, Xinxiang Medical University, Xinxiang, Henan 453003

Received:2020-08-25 Revised:2020-10-18 Published:2020-10-22
Contact: Xueliang Liu, Daoshan Yang
Supported by:
the Natural Science Foundation of Shandong Province(ZR2016JL012); the Scientific Research Foundation of Qingdao University of Science and Technology.()

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Abstract

An efficient and convenient copper-catalyzed cascade synthesis of C-4 phosphonated isoquinolin-1(2 H)-ones has been initially proposed. This is the first example for the construction of phosphine-containing heterocycles through copper-catalyzed Ullmann-type coupling reactions using cyanomethylphosphonates as the building blocks, and it will broaden the strategies of organophosphorus synthesis in the field of organic and pharmaceutical chemistry.

Key words: copper-catalysis, isoquinolin-1(2 H)-one, tandem reaction, organophosphorus

Cite this article

Suyan Zhao, Xueqin Gong, Ziyu Gan, Qiuli Yan, Xueliang Liu, Daoshan Yang. Efficient Copper-Catalyzed Domino Synthesis of Phosphonated Isoquinolin-1(2H)-ones Using Cyanomethylphosphonates as Building Blocks[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 258-266.

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References 12

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Entry	Catalyst	Solvent	Base	Ligand	Isolated yield/%
1	CuCl	DMSO	Na ₂CO ₃	A	67
2	CuCl	DMSO	Na ₂CO ₃	B	24
3	CuCl	DMSO	Na ₂CO ₃	C	61
4	CuCl	DMSO	Na ₂CO ₃	D	23
5	CuCl	DMSO	Na ₂CO ₃	E	15
6	CuCl	DMSO	Na ₂CO ₃	F	18
7	CuCl	DMSO	Na ₂CO ₃	G	5
8	CuCl	DMSO	Na ₂CO ₃	H	Trace
9	CuCl	DMSO	Na ₂CO ₃	I	21
10	CuCl	DMSO	Na ₂CO ₃	None	15
11	CuCl	DMSO	K ₂ CO ₃	A	79
12	CuCl	DMSO	Cs ₂CO ₃	A	76
13	CuCl	DMSO	Pyridine	A	0
14 15	CuCl CuCl	DMSO DMF	t-BuOK K ₂CO ₃	A A	76 65
16	CuCl	Toluene	K ₂CO ₃	A	32
17	CuCl	NMP	K ₂CO ₃	A	57
18	CuI	DMSO	K ₂CO ₃	A	74
19	CuBr	DMSO	K ₂CO ₃	A	63
20	CuCl ₂	DMSO	K ₂CO ₃	A	57
21	Cu(OAc) ₂	DMSO	K ₂CO ₃	A	67
22	CuCl	DMSO	K ₂CO ₃	A	74 ^c
23	CuCl	DMSO	K ₂CO ₃	A	77 ^d

Entry	Catalyst	Solvent	Base	Ligand	Isolated yield/%
1	CuCl	DMSO	Na ₂CO ₃	A	67
2	CuCl	DMSO	Na ₂CO ₃	B	24
3	CuCl	DMSO	Na ₂CO ₃	C	61
4	CuCl	DMSO	Na ₂CO ₃	D	23
5	CuCl	DMSO	Na ₂CO ₃	E	15
6	CuCl	DMSO	Na ₂CO ₃	F	18
7	CuCl	DMSO	Na ₂CO ₃	G	5
8	CuCl	DMSO	Na ₂CO ₃	H	Trace
9	CuCl	DMSO	Na ₂CO ₃	I	21
10	CuCl	DMSO	Na ₂CO ₃	None	15
11	CuCl	DMSO	K ₂ CO ₃	A	79
12	CuCl	DMSO	Cs ₂CO ₃	A	76
13	CuCl	DMSO	Pyridine	A	0
14 15	CuCl CuCl	DMSO DMF	t-BuOK K ₂CO ₃	A A	76 65
16	CuCl	Toluene	K ₂CO ₃	A	32
17	CuCl	NMP	K ₂CO ₃	A	57
18	CuI	DMSO	K ₂CO ₃	A	74
19	CuBr	DMSO	K ₂CO ₃	A	63
20	CuCl ₂	DMSO	K ₂CO ₃	A	57
21	Cu(OAc) ₂	DMSO	K ₂CO ₃	A	67
22	CuCl	DMSO	K ₂CO ₃	A	74 ^c
23	CuCl	DMSO	K ₂CO ₃	A	77 ^d

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以氰甲基亚磷酸酯为含膦试剂的铜催化膦酰化异喹啉酮类化合物的高效合成

Efficient Copper-Catalyzed Domino Synthesis of Phosphonated Isoquinolin-1(2H)-ones Using Cyanomethylphosphonates as Building Blocks

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