Catalyst- and Additive-Free Direct Synthesis of N-Sulfonyl Guanidines

doi:10.6023/cjoc202308019

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1276-1283.DOI: 10.6023/cjoc202308019 Previous Articles Next Articles

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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

麦尔哈巴•居来提^a, 布鲁努尔•玉散^a, 阿不都热合曼•乌斯曼^a^,^b^,^*()

a 新疆师范大学化学化工学院乌鲁木齐 830054
b 新疆储能与光电催化材料重点实验室乌鲁木齐 830054

收稿日期:2023-08-20 修回日期:2023-11-16 发布日期: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

Julaiti Maierhaba^a, Yusan Bulunuer^a, Wusiman Abudureheman^a^,^b()

a School of Chemistry and Chemical Engineering, Xinjiang Normal University, Urumqi 830054
b Xinjiang Key Laboratory of Energy Storage and Photoelectrocatalytic Materials, Urumqi 830054

Received:2023-08-20 Revised:2023-11-16 Published:2023-12-08
Contact: * E-mail: arahman@xjnu.edu.cn
Supported by:
Natural Science Foundation of Xinjiang Uygur Autonomous Region(2021D01A115); Xinjiang Key Laboratory of Energy Storage and Photoelectrocatalytic Materials(XJDX1709-2022-02)

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Abstract

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

Cite this article

Julaiti Maierhaba, Yusan Bulunuer, Wusiman Abudureheman. Catalyst- and Additive-Free Direct Synthesis of N-Sulfonyl Guanidines[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1276-1283.

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References 37

[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. pmid: 1542101
[3]	Buxbaum A.; Kratzer C.; Graninger W.; Georgopoulos A. J. Antimicrob. Chemother. 2006, 58, 193. doi: 10.1093/jac/dkl206
[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. doi: 10.1039/c2cs15288f
[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. doi: 10.1248/cpb.58.1555
[9]	Berlinck R. G. S. Nat. Prod. Rep. 1999, 16, 339. doi: 10.1039/a900338j
[10]	Berlinck R. G, Trindade-Silva A. E.; Santos M. F. Nat. Prod. Rep. 2012, 29, 1382. doi: 10.1039/c2np20071f pmid: 22991131
[11]	Berlinck R. G.; Romminger S. Nat. Prod. Rep, 2016, 33, 456. doi: 10.1039/c5np00108k pmid: 26689539
[12]	Selig P. Guanidines as Reagents and Catalysts II, Vol. 51, Springer, Cham, Switzerland, 2017.
[13]	Saczewski F.; Balewski Ł. Expert. Opin. Ther. Pat. 2009, 19, 1417. doi: 10.1517/13543770903216675
[14]	Bailey P. J.; Pace S. Coord. Chem. Rev. 2001, 214, 91. doi: 10.1016/S0010-8545(00)00389-1
[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. doi: 10.1016/j.bioorg.2023.106600
[17]	Zhang W. X.; Xu L.; Xi Z. Chem. Commun. 2015, 51, 254. doi: 10.1039/C4CC05291A
[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. doi: 10.1039/c4cs00013g pmid: 24626874
[20]	Wang L.; Chi Y.; Zhang W.; Xi Z. Chin. J. Org. Chem. 2018, 38, 1341. (in Chinese) doi: 10.6023/cjoc201801037
	(王连军, 迟樾, 张文雄, 席振峰, 有机化学, 2018, 38, 1341.) doi: 10.6023/cjoc201801037
[21]	Gao Y.; Carta V.; Pink M.; Smith J. M. J. Am. Chem. Soc. 2021, 143, 5324. doi: 10.1021/jacs.1c02068
[22]	Karmakar H.; Anga S.; Panda T. K.; Chandrasekhar V. RSC Adv. 2022, 12, 4501. doi: 10.1039/d2ra00242f pmid: 35425514
[23]	Zhang Z.; Chang W. Chin. J. Org. Chem. 2021, 41, 1835. (in Chinese)
	(张震, 畅温旭, 有机化学, 2021, 41, 1835.) doi: 10.6023/cjoc202010020
[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.; Štrukil V.; Friščić T. Angew. Chem., Int. Ed. 2014, 53, 9321. doi: 10.1002/anie.v53.35
[26]	Zhang Z.; Huang B.; Qiao G.; Zhu L.; Xiao F.; Chen F.; Zhang Z. Angew. Chem., Int. Ed. 2017, 56, 4320. doi: 10.1002/anie.201700539 pmid: 28319297
[27]	Qiao G.; Zhang Z.; Huang B.; Zhu L.; Xiao F.; Zhang Z. Synthesis 2018, 50, 330. doi: 10.1055/s-0036-1588576
[28]	Bossio R.; Marcaccini S.; Pepino R. Tetrahedron Lett. 1995, 36, 2325. doi: 10.1016/0040-4039(95)00246-9
[29]	Gu Z. Y.; Liu Y.; Wang F.; Bao X.; Wang S. Y.; Ji S. J. ACS Catal. 2017, 7, 3893. doi: 10.1021/acscatal.7b00798
[30]	Fang Y.; Yang J. M.; Zhang R.; Wang S. Y.; Ji S. J. Org. Chem. Front. 2019, 6, 3383. doi: 10.1039/c9qo00815b
[31]	Hazarika D.; Borah A. J.; Phukan P. Chem. Commun. 2019, 55, 1418. doi: 10.1039/C8CC08564A
[32]	Mishra D.; Borah A. J.; Phukan P.; Hazarika D.; Phukan P. Chem. Commun. 2020, 56, 8408. doi: 10.1039/D0CC02430A
[33]	Mishra D.; Rajkhowa S.; Phukan P. iScience 2023, 26, 107258. doi: 10.1016/j.isci.2023.107258
[34]	Rouzi A.; Hudabaierdi R.; Wusiman A. Tetrahedron 2018, 74, 2475. doi: 10.1016/j.tet.2018.03.074
[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. doi: 10.1002/chem.201405014 pmid: 25428578
[37]	Egg H.; Gnauer U.; Hambrusch B. Arch. Pharm. 1987, 320, 673. pmid: 3675162

Entry	1a∶2a	Solvent	Temp./℃	Yield^b/%
1^c	1∶2	DCE	r.t.	Trace
2^c	1∶2	DCE	80	65
3	1∶2	DCE	80	81
4	1∶2	EtOAc	80	Trace
5	1∶2	Dioxane	80	Trace
6	1∶2	MeCN	80	75
7	1∶2	CHCl₃	80	88
8	1∶2	PhCl	80	80
9	1∶2	DMF	80	Trace
10	1∶2	DMSO	80	Trace
11	1∶2	Acetone	80	30
12	1∶2	i-PrOH	80	78
13	1∶2	DCM	80	50
14	1∶2	CHCl₃	60	72
15	1∶1.5	CHCl₃	80	90
16	1∶1.2	CHCl₃	80	85
17^d	1∶1.2	CHCl₃	100	91
18	1∶1.1	CHCl₃	100	82

Entry	1a∶2a	Solvent	Temp./℃	Yield^b/%
1^c	1∶2	DCE	r.t.	Trace
2^c	1∶2	DCE	80	65
3	1∶2	DCE	80	81
4	1∶2	EtOAc	80	Trace
5	1∶2	Dioxane	80	Trace
6	1∶2	MeCN	80	75
7	1∶2	CHCl₃	80	88
8	1∶2	PhCl	80	80
9	1∶2	DMF	80	Trace
10	1∶2	DMSO	80	Trace
11	1∶2	Acetone	80	30
12	1∶2	i-PrOH	80	78
13	1∶2	DCM	80	50
14	1∶2	CHCl₃	60	72
15	1∶1.5	CHCl₃	80	90
16	1∶1.2	CHCl₃	80	85
17^d	1∶1.2	CHCl₃	100	91
18	1∶1.1	CHCl₃	100	82

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

Catalyst- and Additive-Free Direct Synthesis of N-Sulfonyl Guanidines

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References 37

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