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Facile one-pot synthesis of tetrasubstituted N-sulfonylguanidines from sulfonamides and ureas

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Abstract

A facile method for the synthesis of tetrasubstituted N-sulfonylguanidines has been developed via the direct condensation of sulfonamides and ureas in the presence of phosphoryl chloride under basic conditions. Detailed synthetic studies showed that this is a simple protocol for preparing N-sulfonylguanidines at room temperature in a short reaction time with good to excellent yields.

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References

  1. Alonso-Moreno C, Antinolo A, Carrillo-Hermosilla F, Otero A (2014) Chem Soc Rev 43:3406

    Article  CAS  PubMed  Google Scholar 

  2. Zhang WX, Xu L, Xi Z (2015) Chem Commun 51:254

    Article  Google Scholar 

  3. Taylor JE, Bull SD, Williams JMJ (2012) Chem Soc Rev 41:2109

    Article  CAS  PubMed  Google Scholar 

  4. Ishikawa T, Kumamoto T (2006) Synthesis 5:737

    Article  CAS  Google Scholar 

  5. Kumamoto T, Ishikawa I (2009) Superbases for organic synthesis: guanidines, amidines, phosphazenes and related organoctalysts. John Wiley & Sons, West Sussex

    Google Scholar 

  6. Ishikawa T (2010) Chem Pharm Bull 58:1555

    Article  CAS  Google Scholar 

  7. Berlinck RGS (1999) Nat Prod Rep 16:339

    Article  CAS  Google Scholar 

  8. Berlinck RG, Trindade-Silva AE, Santos MF (2012) Nat Prod Rep 29:1382

    Article  CAS  PubMed  Google Scholar 

  9. Berlinck RG, Romminger S (2016) Nat Prod Rep 33:456

    Article  CAS  PubMed  Google Scholar 

  10. Shaw JW, Grayson DH, Rozas I (2015) Guanidines as reagents and catalysts I. In: Selig P (ed) Topics in heterocyclic chemistry, vol 50. Springer, Berlin, p 1

    Google Scholar 

  11. Saczewski F, Balewski Ł (2009) Expert Opin Ther Pat 19:1417

    Article  CAS  PubMed  Google Scholar 

  12. Bailey PJ, Pace S (2001) Coord Chem Rev 214:91

    Article  CAS  Google Scholar 

  13. Martyn Coles P (2006) Dalton Trans 985

  14. Guthner T, Mertschenk B, Schulz B (2006) Guanidine and derivatives. Ullmann’s encyclopedia of industrial chemistry, vol 17. Wiley-VCH, Weinheim, p 175

    Google Scholar 

  15. Muller GW, Walters DE, DuBois GE (1992) J Med Chem 35:740

    Article  CAS  PubMed  Google Scholar 

  16. Buxbaum A, Kratzer C, Graninger W, Georgopoulos A, Antimicrob J (2006) Chemother 58:193

    CAS  Google Scholar 

  17. Maksic M, Glasovac Z (2005) Preparation of N, N’, N’’-tris-(3-dimethylaminopropyl)-guanidine from carbodiimide and application in reactions of transesterification of oil. Chem Abstr 143:422044 (WO Patent 2005100306)

    Google Scholar 

  18. Katritzky AR, Rogovoy BV (2005) ARKIVOC 4:49 (and references therein)

    Article  Google Scholar 

  19. Qi Y, Gao H, Yang M, Xia CG, Suo J (2003) Synth Commun 33:1073

    Article  CAS  Google Scholar 

  20. Azzam RA (2019) J Heterocycl Chem 56:619

    Article  CAS  Google Scholar 

  21. Qiao G, Zhang Z, Huang B, Zhu L, Xiao F, Zhang Z (2018) Synthesis 50:330

    Article  CAS  Google Scholar 

  22. Donohue SR, Pike VW, Finnema SJ, Truong P, Andersson J, Gulyás B, Halldin C (2008) J Med Chem 51:5608

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Tan D, Mottillo C, Katsenis AD, Štrukil V, Friščić T (2014) Angew Chem Int Ed 53:9321

    Article  CAS  Google Scholar 

  24. Fang Y, Yang JM, Zhang R, Wang SY, Ji SJ (2019) Org Chem Front 6:3383

    Article  CAS  Google Scholar 

  25. Gu ZY, Liu Y, Wang F, Bao X, Wang SY, Ji SJ (2017) ACS Catal 7:3893

    Article  CAS  Google Scholar 

  26. Deprez P, Vevert JP (1996) Synth Commun 26:4299

    Article  CAS  Google Scholar 

  27. Zhang J, Shi Y (2000) Tetrahedron Lett 41:8075

    Article  CAS  Google Scholar 

  28. Bossio R, Marcaccini S, Pepino R (1995) Tetrahedron Lett 36:2325

    Article  CAS  Google Scholar 

  29. Lange JH, Verhoog S, Sanders HJ, van Loevezijn A, Kruse CG (2011) Tetrahedron Lett 52:3198

    Article  CAS  Google Scholar 

  30. Kharul RK, Goswami A, Gite A, Godha AK, Jain M, Patel PR (2008) Synth Commun 38:1703

    Article  CAS  Google Scholar 

  31. Lange JH, den Hartog AP, van der Neut MA, van Vliet BJ, Kruse CG (2009) Bioorg Med Chem Lett 19:5675

    Article  CAS  PubMed  Google Scholar 

  32. Hazarika D, Borah AJ, Phukan P (2019) Chem Commun 55:1418

    Article  CAS  Google Scholar 

  33. Chorvat RJ, Berbaum J, Seriacki K, McElroy JF (2012) Bioorg Med Chem Lett 22:6173

    Article  CAS  PubMed  Google Scholar 

  34. Senning A (1967) Acta Chem Scan 21:1293

    Article  CAS  Google Scholar 

  35. Gluszok S, Goossens L, Depreux P, Hénichart JP (2006) Tetrahedron Lett 47:6087

    Article  CAS  Google Scholar 

  36. Yang W, Huang D, Zeng X, Luo D, Wang X, Hu Y (2018) Chem Commun 54:8222

    Article  CAS  Google Scholar 

  37. Aswad M, Chiba J, Hatanaka Y, Tomohiro T (2019) Tetrahedron Lett 60:1611

    Article  CAS  Google Scholar 

  38. Han J, Zhou R, Huang C, Zeng Q, Long Q, Zhang Q, Liu M (2019) Tetrahedron Lett 60:151285

    Article  CAS  Google Scholar 

  39. Rouzi A, Hudabaierdi R, Wusiman A (2018) Tetrahedron 74:2475

    Article  CAS  Google Scholar 

  40. Wusiman A, Hudabaierdi R (2017) Synth Commun 47:2015

    Article  CAS  Google Scholar 

  41. Gauvreau JR, Martin GJ (1983) J Chem Soc Perkin Trans 2(9):1541

    Article  Google Scholar 

  42. Roizen JL, Zalatan DN, Bois JD (2013) Angew Chem Int Ed 52:11343

    Article  CAS  Google Scholar 

  43. Bouchareb F, Boufas W, Cheloufi H, Berredjem M, Aouf NE (2014) Phosphorus, Sulfur Silicon Relat Elem 189:587

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (No: 21762044) and Natural Science Foundation of the Xinjiang Uygur Autonomous Region (No: 2021D01A115).

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Author notes

  1. Fei Wang and Abulimiti Yumaier contributed equally to this work.

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Xinjiang Normal University, Urumqi, 830054, People’s Republic of China

    Fei Wang & Abudureheman Wusiman

  2. College of Chemistry and Environmental Science, Kashi University, Kashi, 844007, People’s Republic of China

    Abulimiti Yumaier & Abudureheman Wusiman

Authors
  1. Fei Wang
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  2. Abulimiti Yumaier
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  3. Abudureheman Wusiman
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Correspondence to Abudureheman Wusiman.

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Wang, F., Yumaier, A. & Wusiman, A. Facile one-pot synthesis of tetrasubstituted N-sulfonylguanidines from sulfonamides and ureas. Monatsh Chem 152, 993–999 (2021). https://doi.org/10.1007/s00706-021-02815-6

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  • DOI: https://doi.org/10.1007/s00706-021-02815-6

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