SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 11: 3960 - 3965

DOI: https://doi.org/10.6023/cjoc202304022

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

  • Haojie Ma ,
  • Fengyuan Zhou ,
  • Fanwen Su ,
  • Bo Han ,
  • Ran Li ,
  • Yuqi Zhang ,
  • Jijiang Wang
Expand
  • 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
* E-mail: ;

Received date: 2023-04-18

  Revised date: 2023-06-06

  Online published: 2023-07-06

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

Fold

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 . DOI: 10.6023/cjoc202304022

References

[1]
(a) Nagaraaj, P.; Vijayakumar, V. Org. Chem. Front. 2019, 6, 2570.
[1]
(b) Zeng, Ch. F.; He, Y.; Li, Q.; Dong, L. Chin. J. Org. Chem. 2023, 43, 1115. (in Chinese)
[1]
(曾成富, 何媛, 李清, 董琳, 有机化学, 2023, 43, 1115.)
[1]
(c) Yin, J. W.; Zhang, J. Y.; Cai, C. Q.; Deng, G. J.; Gong, H. Org. Lett. 2019, 21, 387.
[1]
(d) Zheng, Y. L.; Newman, S. G. ACS Catal. 2019, 9, 4426.
[1]
(e) Dong, H.; Hou, M. F. Chin. J. Org. Chem. 2017, 37, 267. (in Chinese)
[1]
(董浩, 侯梅芳, 有机化学, 2017, 37, 267.)
[1]
(f) Wang, J.; Ren, J. M.; Zhu, Y. P.; Sun, X. Q.; Hu, P. F.; Mu, X.; Zeng, B. B. Tetrahedron Lett. 2023, 116, 154312.
[1]
(g) Tian, Q. Q.; Gan, Z. J.; Wang, X. T.; Li, D.; Luo, W.; Wang, H. J.; Dai, Z. S.; Yuan, J. Y. Molecules 2018, 23, 2234.
[1]
(h) Ye, D. F.; Chen, H.; Liu, Z. Y.; Lei, C. H. Chin. J. Org. Chem. 2021, 41, 1658. (in Chinese)
[1]
(叶丹锋, 陈浩, 刘志园, 雷川虎, 有机化学, 2021, 41, 1658.)
[1]
(i) Lanigan, R. M.; Starkov, P.; Sheppard, T. D. J. Org. Chem. 2013, 78, 4512.
[2]
(a) Walsh, C. T.; O’Brien, R. V.; Khosla, C. Angew. Chem., Int. Ed. 2013, 52, 7098.
[2]
(b) Todorovic, M.; Perrin, D. M. Pept. Sci. 2020, 17, 3895.
[2]
(c) Sheng, G.Z.; Zhang, W. Chin. J. Org. Chem. 2013, 33, 2271. (in Chinese)
[2]
(盛国柱, 张炜, 有机化学, 2013, 33, 2271.)
[2]
(d) Chapman, R. S. L.; Lawrence, R.; Williams, J. M. J.; Bull, S. D. Org. Lett. 2017, 19, 4908.
[2]
(e) Gerack, C. J.; McElwee-White, L. Molecules 2014, 19, 7689.
[3]
(a) Li, Z. Y.; Chen, Y. Z.; Wan, N.W. Chin. J. Synth. Chem. 2022, 30, 419. (in Chinese)
[3]
(李正一, 陈永正, 万南微, 合成化学, 2022, 30, 419.)
[3]
(b) Chen, J.; Jia, J.; Guo, Z.; Zhang, J.; Xie, M. Tetrahedron Lett. 2019, 60, 1426.
[3]
(c) Tan, C.; Liu, Y. G.; Liu, X. Y.; Jia, H. X.; Xu, K.; Huang, S. H.; Wang, J. W.; Tan, J. J. Org. Chem. Front. 2020, 7, 780.
[4]
(a) Reddy, T. N.; Beatriz, A.; Rao, V. J.; Lima, D. P. Chem.-Asian J. 2019, 14, 344.
[4]
(b) Lundberg, H.; Tinnis, F.; Selander, N.; Adolfsson, H. Chem. Soc. Rev. 2014, 43, 2714.
[4]
(c) Pattabiraman, V. R.; Bode, J. W. Nature 2011, 480, 471.
[4]
(d) Yan, Y. Z.; Niu, B.; Xu, K.; Yu, J. H.; Zhi, H. H.; Liu, Y. Q. Adv. Synth. Catal. 2016, 358, 212.
[5]
Hinz, B.; Cheremina, O.; Brune, K. FASEB J. 2008, 22, 383.
[6]
Perez-Aso, M.; Montesinos, M. C.; Mediero, A.; Wilder, T.; Schafer, P. H. Arthritis Res. Ther. 2015, 17, 249.
[7]
Abe, H.; Kikuchi, S.; Hayakawa, K.; Iida, T.; Nagahashi, N.; Maeda, K. ACS Med. Chem. Lett. 2011, 2, 320.
[8]
Primiano, G.; Vollono, C.; Dono, F.; Servidei, S. Epilepsy Res. 2018, 139, 135.
[9]
Mahesh, S.; Tang, K. C.; Raj, M. Molecules 2018, 23, 2615.
[10]
Young, I. S.; Glass, A. L.; Cravillion, T.; Han, C.; Zhang, H.; Gosselin, F. Org. Lett. 2018, 20, 3902.
[11]
Dander, J. E.; Baker, E. L.; Garg, N. K. Chem. Sci. 2017, 8, 6433.
[12]
Pelletier, G.; Powell, D. A. Org. Lett. 2006, 8, 6031.
[13]
Shekhar, A. C.; Kumar, A. R.; Sathaiah, G.; Paul, V. L.; Sridhar, M.; Rao, P. S. Tetrahedron Lett. 2009, 50, 7099.
[14]
(a) Li, Y.; Jia, F.; Li, Z. Chem.-Eur. J. 2013, 19, 82.
[14]
(b) Becerra-Figueroa, L.; Ojeda-Porras, A.; Gamba-Sanchez, D. J. Org. Chem. 2014, 79, 4544.
[15]
Bon, E.; Bigg, D. C. H.; Bertrand, G. J. Org. Chem. 1994, 59, 4035.
[16]
Jiang, H.; Hu, Z.; Gan, C.; Sun, B.; Kong, S.; Bian, F. J. Mol. Catal. 2021, 504, 111490.
[17]
Shah, N.; Gravel, E.; Jawale, D. V.; Doris, E.; Namboothiri, I. N. N. ChemCatChem 2014, 6, 2201.
[18]
Zhang, L.; Han, Z.; Zhao, X.; Wang, Z.; Ding, K. Angew. Chem., Int. Ed. 2015, 54, 6186.
[19]
Lenstra, D. C.; Nguyen, D. T.; Mecinovi?, J. Tetrahedron, 2015, 71, 5547.
[20]
Kong, X.; Xu, B. Org. Lett. 2018, 20, 4495.
[21]
Pathare, S. P.; Jain, A. K. H.; Akamanchi, K. G. RSC Adv. 2013, 21, 7697.
[22]
Rasheed, S.; Rao, D. N.; Reddy, A. S.; Shankar, R.; Das, P. RSC Adv. 2015, 5, 10567.
[23]
Karami, B.; Farahi, M.; Pam, F. Tetrahedron Lett. 2014, 55, 6292.
[24]
Allen, C. L.; Atkinson, B. N.; Williams, J. M. J. Angew. Chem., Int. Ed. 2012, 51, 1383.
[25]
Laconde, G.; Amblard, M.; Martinez, J. Eur. J. Org. Chem. 2019, 2019, 85.
[26]
Sonawane, R. B.; Rasal, N. K.; Jagtap, S. V. Org. Lett. 2017, 19, 2078.
[27]
Sonawane, R. B.; Rasal, N. K.; Bhange, D. S.; Jagtap, S. V. ChemCatChem 2018, 10, 3907.
[28]
(a) Kumar, V.; Dhawan, S.; Girase, P. S.; Singh, P.; Karpoormath, R. Eur. J. Org. Chem. 2021, 2021, 5627.
[28]
(b) Girase, P. S.; Kumar, V.; Dhawan, S.; Karpoormath, R. ChemistrySelect 2022, 7, 3237.
[28]
(c) Acosta-Guzmán, P.; Mateus-Gómez, A.; Gamba-Sánchez, D. Molecules 2018, 23, 2382.
[28]
(d) Yan, Y. Z.; Cui, C.; Li, Z. Chin. J. Org. Chem. 2018, 38, 2501. (in Chinese)
[28]
(闫溢哲, 崔畅, 李政, 有机化学, 2018, 38, 2501.)
[29]
Rao, S. N.; Mohan, D. C.; Adimurthy, S. Tetrahedron 2016, 72, 4889.
[30]
Mahajan, S.; Slathia, N.; Kapoor, K. K. Tetrahedron Lett. 2020, 61, 151859.
[31]
Zhou, Z. J.; Kweon, J.; Jung, H.; Kim, D.; Seo, S.; Chang, S. J. Am. Chem. Soc. 2022, 144, 9161.
[32]
Lakshmi, V. M.; Hsu, F. F.; Davis, B. B.; Zenser, T. V. Chem. Res. Toxicol. 2001, 14, 312.
[33]
Wang, J. K.; Zong, Y. X.; Wang, X. C.; Hu, Y. L.; Yue, G. R. Chin. Chem. Lett. 2015, 26, 1376.
Options
Outlines

/

〈 〉