Iodine-Promoted Transamidation of N,N-Dimethylacetamide (DMA) with Amines

doi:10.6023/cjoc202304022

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (11): 3960-3965.DOI: 10.6023/cjoc202304022 Previous Articles Next Articles

碘促进N,N-二甲基乙酰胺(DMA)与胺的转酰胺反应

马豪杰^*(), 周风院, 苏凡文, 韩波, 李然, 张玉琦^*(), 王记江

延安大学化学与化工学院陕西省化学反应工程重点实验室新能源与新功能材料重点实验室陕西延安 716000

收稿日期:2023-04-18 修回日期:2023-06-06 发布日期:2023-07-05
基金资助:
国家自然科学基金(31701679); 陕西省科学技术协会青年人才托举计划(20220609); 陕西省科技资源开放共享平台(2021PT-004); 延安市科技计划(2022SLSFGG-005); 延安市科学技术协会青年人才托举计划(8); 延安大学大学生创新创业训练计划(D2021032); 延安大学产学研合作培育(CXY202102); 陕西省教育厅青年创新团队(23JP193); 陕西高校青年创新团队资助项目

Iodine-Promoted Transamidation of N,N-Dimethylacetamide (DMA) with Amines

Haojie Ma(), Fengyuan Zhou, Fanwen Su, Bo Han, Ran Li, Yuqi Zhang(), Jijiang Wang

Key Laboratory of New Energy & New Functional Materials, Shaanxi Key Laboratory of Chemical Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an, Shaanxi 716000

Received:2023-04-18 Revised:2023-06-06 Published:2023-07-05
Contact: * E-mail: mahj@yau.edu.cn; yqzhang@iccas.ac.cn
Supported by:
National Natural Science Foundation of China(31701679); Young Talent Fund of Association for Science and Technology in Shaanxi(20220609); Open Sharing Platform for Scientific and Technological Resources of Shaanxi Province(2021PT-004); Yan'an Science and Technology Planning Project(2022SLSFGG-005); the Young Talent Fund of Association for Science and Technology in Yanan(8); Yan'an University Training Program of Innovation and Entrepreneurship for Undergraduates(D2021032); Yan'an University Industry-University-Research Co-operative Cultivation Project(CXY202102); Youth Innovation Team Project of Shaanxi Provincial Education Department(23JP193); Youth Innovation Team of Shaanxi Universities

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Abstract

A novel and convenient transamidation of N,N-dimethylacetamide (DMA) with amines for the synthesis of acetamides with moderate to excellent yields is reported. Low-cost I₂ is used as efficient promoter for this transformation. Furthermore, the reaction has simple conditions, good functional group tolerance, substrates without prefunctionalization, and practicality, which can be widely used in the synthesis of acetamide drugs and biologically active molecules.

Key words: iodine, N-acylation, transamidation, N, N-dimethylacetamide, acetamide

Cite this article

Haojie Ma, Fengyuan Zhou, Fanwen Su, Bo Han, Ran Li, Yuqi Zhang, Jijiang Wang. Iodine-Promoted Transamidation of N,N-Dimethylacetamide (DMA) with Amines[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3960-3965.

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Fig. & Tab. 7

Figure 1. Acetamides structural units in some drug molecules

Scheme 1. Approaches toward acetamides

Entry	I₂/equiv.	Atmosphere	Temp./℃	Yield^b/%
1	1.0	Air	140	31
2	1.0	O₂	140	Trace
3	1.0	N₂	140	54
4	0.5	N₂	140	90
5	1.5	N₂	140	40
6	0.2	N₂	140	36
7	0.1	N₂	140	30
8	0.5	N₂	120	61
9	0.5	N₂	160	68
10^c	0.5	N₂	120	24

Table 1. Optimization of the reaction conditionsa

Table 2. Substrate scope of the I2-promoted transamidation of DMA with aminesa

Scheme 2. Gram scale reaction

Scheme 3. Control experiments

Scheme 4. Proposed mechanism

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碘促进N,N-二甲基乙酰胺(DMA)与胺的转酰胺反应

Iodine-Promoted Transamidation of N,N-Dimethylacetamide (DMA) with Amines

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Fig. & Tab. 7

References 33

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