Convenient one-pot synthesis of sulfonamides from thiols using trichloroisocyanuric acid

Synthetic Communications

Volumn 37, Issue 12, 2007, Pages 2039-2050

  Bonk, Jason D ^a,b   Amos, David T ^a   Olson, Sarah J ^a  

^a 3M COMPANY   (United States)

^b 3M Center   (United States)

Author keywords

Oxidation; Sulfonamides; Thiol; Trichloroisocyanuric acid

Indexed keywords

AMMONIUM CHLORIDE; CHLORIDE; CYANURIC ACID; SULFONAMIDE; THIOL DERIVATIVE; TRIETHYLAMINE;

ARTICLE; CHEMICAL REACTION; ONE POT SYNTHESIS; OXIDATION;

EID: 34250316483     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701356942     Document Type: Article

References (12)

1. Bonk, J. D.; Dellaria, J. F., Jr. International Patent Publ. WO 2005/066169.
2. Hays, D. S.; Danielson, M. E.; Gerster, J. F.; Niwas, S.; Kshirsagar, T. A.; Heppner, P. D.; Moser, W. H.; Moseman, J. T.; Radmer, M. R.; Kavanagh, M. A.; Strong, S. A.; Bonk, J. D International Patent Publ. WO 2005/079195.
3. Douglass, I. B.; Johnson, T. B. Interaction of chlorine with different types of organic sulfur compounds. J. Am. Chem. Soc. 1938, 60, 1486-1489.
4. Meinzer, A.; Breckel, A.; Thaher, B. A.; Manicone, N.; Otto, H.-H. Properties and reactions of substituted 1,2-thiazetidine 1,1-dioxides: Chiral mono- and bicyclic 1,2-thiazetidine 1,1-dioxides from a-amino acids. Helv. Chim. Acta 2004, 87, 90-105.
5. Skulnick, H. I.; Johnson, P. D.; Aristoff, P. A.; Morris, J. K.; Lovasz, K. D.; Howe, W. J.; Watenpaugh, K. D.; Janakiraman, M. N.; Anderson, D. J.; Reischer, R. J.; Schwartz, T. M.; Banitt, L. S.; Tomich, P. K.; Lynn, J. C.; Horng, M.-M.; Chong, K.-T.; Hinshaw, R. R.; Dolak, L. A.; Seest, E. P.; Schwende, F. J.; Rush, B. D.; Howard, G. M.; Toth, L. N.; Wilkinson, K. R.; Kakuk, T. J.; Johnson, C. W.; Cole, S. L.; Zaya, R. M.; Zipp, G. L.; Possert, P. L.; Dalga, R. J.; Zhong, W.-Z.; Williams, M. G.; Romines, K. R. Structure-based design of nonpeptidic HIV protease inhibitors: The sulfonamide-substituted cyclooctylpyranones. J. Med. Chem. 1997, 40, 1149-1164.
6. Vedejs, E.; Kongkittingam, C. Solution-phase synthesis of a hindered N-methylated tetrapeptide using Bts-protected amino acid chlorides: Efficient coupling and methylation steps allow purification by extraction. J. Org. Chem. 2000, 65, 2309-2318.
7. Youssef, K. M.; Al-Abdullah, E.; El-Khamees, H. Synthesis of certain diarylsulfonylureas as antitumor agents. Med. Chem. Res. 2001, 10, 404-418.
8. Park, Y. J.; Shin, H. H.; Kim, Y. H. Convenient one-pot synthesis of sulfonyl chlorides from thiols using sulfuryl chloride and metal nitrate. Chem. Lett. 1992, 1483-1486.
9. Wright, S. W.; Hallstrom, K. N. A convenient preparation of heteroaryl sulfonamides and sulfonyl fluorides from heteroaryl thiols. J. Org. Chem. 2006, 71, 1080-1084.
10. Tilstam, U.; Weinmann, H. Trichloroisocyanuric acid: A safe and efficient oxidant. Org. Process Res. Dev. 2002, 6, 384-393.
11. Roblin, R. O., Jr.; Clapp, J. W. The preparation of heterocyclic sulfonamides. J. Am. Chem. Soc. 1950, 72, 4890-4892.
12. Zhong, P.; Guo, M.-P. Preparation of disulfides by the oxidation of thiols using trichloroisocyanuric acid. Synth. Commun. 2001, 31, 1825-1828.