非金属1,8-二氮杂双环[5.4.0]十一碳-7-烯介导下乙缩醛酸与异硫氰酸酯反应合成α-缩醛基酰胺
收稿日期: 2024-03-20
修回日期: 2024-04-08
网络出版日期: 2024-04-30
基金资助
山东省自然科学基金(ZR2021MB065); 青海省科技国际合作专项(2022-HZ-813)
Metal-Free 1,8-Diazabicyclo(5.4.0)-undec-7-ene Mediated Synthesis of α-Acetal Amides through Reaction of Glyoxylic Acid Acetalde with Aryl Isothiocyanates
Received date: 2024-03-20
Revised date: 2024-04-08
Online published: 2024-04-30
Supported by
Natural Science Foundation of Shandong Province(ZR2021MB065); Science and Technology International Cooperation Project of Qinghai Province(2022-HZ-813)
丁柔 , 石思雨 , 马超 , 魏伟 , 吕玉芬 . 非金属1,8-二氮杂双环[5.4.0]十一碳-7-烯介导下乙缩醛酸与异硫氰酸酯反应合成α-缩醛基酰胺[J]. 有机化学, 2024 , 44(7) : 2216 -2222 . DOI: 10.6023/cjoc202403029
Metal-free condensation reaction of glyoxylic acid acetalde with aryl isothiocyanates leading to α-acetal amides has been reported. The present protocol, which simply utilizes 1,8-diazabicyclo(5.4.0)-undec-7-ene (DBU) as base, provides a green and efficient approach to construct a series of α-acetal amides in the absence of metal catalysts and stoichiometric amounts of coupling reagents.
Key words： metal-free; α-acetalamide; glyoxylic acid; aryl isothiocyanate
| [1] | (a) Jia, L. Q.; Jiang, H. F.; Li, J. H. Chem Commun. 1999, 985. |
| [1] | (b) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617. |
| [1] | (c) Francke, W.; Kitching, W. Curr. Org. Chem. 2001, 5, 233. |
| [1] | (d) Brimble, M. A.; Furkert, D. P. Curr. Org. Chem. 2003, 7, 1461. |
| [1] | (f) Favre, S.; Vogel, P.; Gerber-Lemaire, S. Molecules 2008, 13, 2570. |
| [1] | (g) Booth, Y. K.; Kitching, W.; De Voss, J. J. Nat. Prod. Rep. 2009, 26, 490. |
| [2] | (a) Suffis, R.; Morton, L. B.; Ishida, K.; Sawano, K.; VanLoveren, A. G.; Tetsuo, N.; Green, C. B.; Reitz, G. A.; Kang, R. K. L.; Sato, T. US 5626852, 1997[Chem. Abstr. 1997, 127, 23502]. |
| [2] | (b) Ajaikumar, S.; Pandurangan, A. J. Mol. Catal. A: Chem 2008, 290, 35. |
| [3] | (a) Quach, R.; Chorley, D. F.; Brimble, M. A. Org. Biomol. Chem. 2014, 12, 7423. |
| [3] | (b) Lenci, E.; Menchi, G.; Saldívar-Gonzalez, F. I.; Medina-Franco, J. L.; Trabocchi, A. Org. Biomol. Chem. 2019, 17, 1037. |
| [3] | (c) Gozlan, C.; Deruer, E.; Duclos, M.-C.; Molinier, V.; Aubry, J.-M.; Redl, A.; Dugueta, N.; Lemaire, M. Green Chem. 2016, 18, 1994. |
| [4] | (a) Torok, D. S.; Fifueroa, J. J.; Scott, W. J. J. Org. Chem. 1993, 58, 7274. |
| [4] | (b) Shen, Y.-X.; Jiang, H.-F.; Wang, Z.-Y. Chin. J. Org. Chem. 2008, 28, 782. (in Chinese) |
| [4] | (申艳霞, 江焕峰, 汪朝阳, 有机化学, 2008, 28, 782.) |
| [5] | Zhang, S.; Tan, Z.; Zhang, H.; Liu, J.; Xua, W.; Xu, K. Chem. Commun. 2017, 53, 11642. |
| [6] | Xiang, P.; He, L.; Li, H.; Qi, Z.; Zhang, M.; Fu, Q.; Wei, J.; Du, X.; Yi, D.; Wei, S. Tetrahedron Lett. 2020, 61, 152369. |
| [7] | Lyu, X.-L.; Huang, S.-S.; Song, H.-J.; Liu, Y.-X.; Wang, Q.-M. RSC Adv. 2019, 9, 36213. |
| [8] | Ma, C.-H.; Ji, Y.; Zhao, J.; He, X.; Zhang, S.-T.; Jiang, Y.-Q.; Yu, B. Chin. J. Catal. 2022, 43, 571. |
| [9] | Zhang, M.; Nan, G.; Zhao, X.; Wei, W. Chin. J. Org. Chem. 2022, 42, 4315. (in Chinese) |
| [9] | (张孟琪, 南光明, 赵晓辉, 魏伟, 有机化学, 2022, 42, 4315.) |
| [10] | Kim, S.; Park, B.; Lee, G. S.; Hong, S. H. J. Org. Chem. 2023, 88, 6532. |
| [11] | (a) Nagaraaj, P.; Vijayakumar, V. Org. Chem. Front. 2019, 6, 2570. |
| [11] | (b) Zeng, C. F.; He, Y.; Li, Q.; Dong, L. Chin. J. Org. Chem. 2023, 43, 1115. (in Chinese) |
| [11] | (曾成富, 何媛, 李清, 董琳, 有机化学, 2023, 43, 1115.) |
| [11] | (c) Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451. |
| [11] | (d) Papadopoulos, L.; Kluge, M.; Bikiaris, D. N.; Robert, T. Polymers 2020, 12, 980. |
| [11] | (e) Ye, D. F.; Chen, H.; Liu, Z. Y.; Lei, C. H. Chin. J. Org. Chem. 2021, 41, 1658. (in Chinese) |
| [11] | (叶丹锋, 陈浩, 刘志园, 雷川虎, 有机化学, 2021, 41, 1658.) |
| [12] | (a) Walsh, C. T.; O’Brien, R. V.; Khosla, C. Angew. Chem., Int. Ed. 2013, 52, 7098. |
| [12] | (b) Todorovic, M.; Perrin, D. M. Pept. Sci. 2020, 17, 3895. |
| [12] | (c) Chapman, R. S. L.; Lawrence, R.; Williams, J. M. J.; Bull, S. D. Org. Lett. 2017, 19, 4908. |
| [12] | (d) Gerack, C. J.; McElwee-White, L. Molecules 2014, 19, 7689. |
| [13] | (a) Chen, J.; Jia, J.; Guo, Z.; Zhang, J.; Xie, M. Tetrahedron Lett. 2019, 60, 1426. |
| [13] | (b) Santos, A. S.; Silva, A. M. S.; Marques, M. M. B. Eur. J. Org. Chem. 2020, 2501. |
| [13] | (c) Dorr, B. M.; Fuerst, D. E. Curr. Opin. Chem. Biol. 2018, 43, 127. |
| [14] | (a) Vaughan, W. R.; Andersen, M. V.; Blanchard, H. S.; Mccane, D. I.; Meyer W. L. J. Org. Chem. 1955, 20, 819. |
| [14] | (b) Losse, V. G.; Weddige, H. Justus Liebigs Ann. Chem. 1960, 636, 144. |
| [14] | (c) Delaveau, V.; Mouloungui, Z.; Gaset, A. Synth. Commun. 1996, 26, 2341. |
| [14] | (d) Li, Y.; Chen, W.; Zhao, L.; Zhang, J.-Q.; Zhao, Y.; Li, C.; Guo, B.; Tang, L.; Yang, Y.-Y. RSC Adv. 2022, 12, 20550. |
| [15] | (a) 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. |
| [15] | (b) Huang, J.; Yang, Y.; Zhang, Z.; Liu, S. Chin. J. Org. Chem. 2024, 44, 409. (in Chinese) |
| [15] | 黄净, 杨毅华, 张占辉, 刘守信, 有机化学, 2024, 44, 409). |
| [15] | (c) Chen, W.; Shao, J.; Hu, M.; Yu, W.; Giulianotti, M. A.; Houghten, R. A.; Yu, Y. Chem. Sci. 2013, 4, 970. |
| [15] | (d) Li, J.-S.; Xie, X.-Y.; Jiang, S.; Yang, P.-P.; Li, Z.-W.; Lu, C.-H.; Liu. W.-D. Org. Chem. Front. 2021, 8, 697. |
| [15] | (e) Tan, J.; Guo, Y.; Zeng, F.; Chen, G.; Xie, L.; He, W. Chin. J. Org. Chem. 2018, 38, 1740. (in Chinese) |
| [15] | (谭家希, 郭也, 曾飞, 陈观荣, 谢龙勇, 何卫民, 有机化学, 2018, 38, 1740.) |
| [15] | (f) Xie, L.-Y.; Peng, S.; Lu, L.-H.; Hu, J.; Bao, W.-H.; Zeng, F.; Tang, Z.; Xu, X.; He, W.-M. ACS Sustainable Chem. Eng. 2018, 6, 7989. |
| [16] | (a) Wang, Z.; Liu, Q.; Liu, R.; Ji, Z.; Li, Y.; Zhao, X.; Wei, W. Chin. Chem. Lett. 2022, 33, 1479. |
| [16] | (b) Wang, Z.; Meng, N.; Lv, Y.; Wei, W.; Yue, H.; Zhong, G. Chin. Chem. Lett. 2023, 34, 107599. |
| [16] | (c) Lv, Y.; Ding, H.; You, J.; Wei, W.; Yi, D. Chin. Chem. Lett. 2024, 35, 109107. |
| [17] | Pinto, A.; Conti, P.; Grazioso, G.; Tamborini, L.; Madsen, U.; Nielsen, B.; De Micheli, C. Eur. J. Med. Chem. 2011, 46, 787. |
/
| 〈 |
|
〉 |
