无催化剂和无添加剂条件下直接合成N-磺酰基胍类化合物
收稿日期: 2023-08-20
修回日期: 2023-11-16
网络出版日期: 2023-12-08
基金资助
新疆维吾尔自治区自然科学基金(2021D01A115); 新疆储能及光电催化材料重点实验室(XJDX1709-2022-02)
Catalyst- and Additive-Free Direct Synthesis of N-Sulfonyl Guanidines
Received date: 2023-08-20
Revised date: 2023-11-16
Online published: 2023-12-08
Supported by
Natural Science Foundation of Xinjiang Uygur Autonomous Region(2021D01A115); Xinjiang Key Laboratory of Energy Storage and Photoelectrocatalytic Materials(XJDX1709-2022-02)
麦尔哈巴?居来提 , 布鲁努尔?玉散 , 阿不都热合曼?乌斯曼 . 无催化剂和无添加剂条件下直接合成N-磺酰基胍类化合物[J]. 有机化学, 2024 , 44(4) : 1276 -1283 . DOI: 10.6023/cjoc202308019
A simple and direct method for the synthesis of N-sulfonyl guanidines from sulfonamide and carbodiimides under catalyst- and additive-free conditions was demonstrated. This method has the advantages of no catalyst and additive required, simple operation, good functional group compatibility, a wide range of substrate applications, high yield, high atomic economy, and the ability to scale up proportionally. It provides a facile and efficient strategy for the preparation of N,N',N''-trisub- stituted sulfonyl guanidines.
Key words： sulfonyl guanidine; sulfonamide; carbodiimide; catalyst-free; additive-free
| [1] | Guthner T.; Mertschenk B.; Schulz B. Guanidine and Derivatives, In Ullmann's Encyclopedia of Industrial Chemistry, 17th ed., Wiley- VCH, Weinheim, 2006, p. 175. |
| [2] | Muller G. W.; Walters D. E.; DuBois G. E. J. Med. Chem. 1992, 35, 740. |
| [3] | Buxbaum A.; Kratzer C.; Graninger W.; Georgopoulos A. J. Antimicrob. Chemother. 2006, 58, 193. |
| [4] | Maksic M.; Glasovac, Z. WO 2005100306, 2005. |
| [5] | Taylor J. E.; Bull S. D.; Williams J. M. J. Chem. Soc. Rev. 2012, 41, 2109. |
| [6] | Ishikawa T.; Kumamoto T. Synthesis 2006, 5, 737. |
| [7] | Kumamoto T.; Ishikawa I.Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organoctalysts, John Wiley & Sons Ltd, Noida, India, 2009, Chapter 10, p. 295. |
| [8] | Ishikawa T. Chem. Pharm. Bull. 2010, 58, 1555. |
| [9] | Berlinck R. G. S. Nat. Prod. Rep. 1999, 16, 339. |
| [10] | Berlinck R. G, Trindade-Silva A. E.; Santos M. F. Nat. Prod. Rep. 2012, 29, 1382. |
| [11] | Berlinck R. G.; Romminger S. Nat. Prod. Rep, 2016, 33, 456. |
| [12] | Selig P. Guanidines as Reagents and Catalysts II, Vol. 51, Springer, Cham, Switzerland, 2017. |
| [13] | Saczewski F.; Balewski ?. Expert. Opin. Ther. Pat. 2009, 19, 1417. |
| [14] | Bailey P. J.; Pace S. Coord. Chem. Rev. 2001, 214, 91. |
| [15] | Coles M. P. Dalton Trans 2006, 985. |
| [16] | Gomes A. R.; Varela C. L.; Pires A. S.; Tavares-da-Silva E. J.; Roleira F. M. Bioorg. Chem. 2023, 138, 106600. |
| [17] | Zhang W. X.; Xu L.; Xi Z. Chem. Commun. 2015, 51, 254. |
| [18] | Katritzky A. R.; Rogovoy B. V. ARKIVOC 2005, 4, 49. |
| [19] | Alonso-Moreno C.; Antinolo A.; Carrillo-Hermosilla F.; Otero A. Chem. Soc. Rev. 2014, 43, 3406. |
| [20] | Wang L.; Chi Y.; Zhang W.; Xi Z. Chin. J. Org. Chem. 2018, 38, 1341. (in Chinese) |
| [20] | (王连军, 迟樾, 张文雄, 席振峰, 有机化学, 2018, 38, 1341.) |
| [21] | Gao Y.; Carta V.; Pink M.; Smith J. M. J. Am. Chem. Soc. 2021, 143, 5324. |
| [22] | Karmakar H.; Anga S.; Panda T. K.; Chandrasekhar V. RSC Adv. 2022, 12, 4501. |
| [23] | Zhang Z.; Chang W. Chin. J. Org. Chem. 2021, 41, 1835. (in Chinese) |
| [23] | (张震, 畅温旭, 有机化学, 2021, 41, 1835.) |
| [24] | Yamamoto I.; Tokanou H.; Uemura H. A.; Gotoh H. J. Chem. Soc., Perkin Trans. 1 1977, 1241. |
| [25] | Tan D.; Mottillo C.; Katsenis A. D.; ?trukil V.; Fri??i? T. Angew. Chem., Int. Ed. 2014, 53, 9321. |
| [26] | Zhang Z.; Huang B.; Qiao G.; Zhu L.; Xiao F.; Chen F.; Zhang Z. Angew. Chem., Int. Ed. 2017, 56, 4320. |
| [27] | Qiao G.; Zhang Z.; Huang B.; Zhu L.; Xiao F.; Zhang Z. Synthesis 2018, 50, 330. |
| [28] | Bossio R.; Marcaccini S.; Pepino R. Tetrahedron Lett. 1995, 36, 2325. |
| [29] | Gu Z. Y.; Liu Y.; Wang F.; Bao X.; Wang S. Y.; Ji S. J. ACS Catal. 2017, 7, 3893. |
| [30] | Fang Y.; Yang J. M.; Zhang R.; Wang S. Y.; Ji S. J. Org. Chem. Front. 2019, 6, 3383. |
| [31] | Hazarika D.; Borah A. J.; Phukan P. Chem. Commun. 2019, 55, 1418. |
| [32] | Mishra D.; Borah A. J.; Phukan P.; Hazarika D.; Phukan P. Chem. Commun. 2020, 56, 8408. |
| [33] | Mishra D.; Rajkhowa S.; Phukan P. iScience 2023, 26, 107258. |
| [34] | Rouzi A.; Hudabaierdi R.; Wusiman A. Tetrahedron 2018, 74, 2475. |
| [35] | Liu A. R.; Zhang L.; Li J.; Wusiman A. RSC Adv. 2021, 25, 15161. |
| [36] | Holthausen M. H.; Colussi M.; Stephan D. W. Chem.-Eur. J. 2015, 21, 2193. |
| [37] | Egg H.; Gnauer U.; Hambrusch B. Arch. Pharm. 1987, 320, 673. |
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