Synthesis of Sulfonylhydrazine-1,2-dicarboxylates from Thiols and Dialkyl Azodicarboxylates

Abstract

1-Sulfonylhydrazine-1,2-dicarboxylates are efficiently prepared via nucleophilic addition of thiols/thiophenols to dialkyl azodicarboxylates and subsequent oxidation with MCPBA. The protocol represents the first application of sulfenylhydrazines as precursors to sulfonylhydrazine derivatives, leading to a novel and effective method for the synthesis of sulfonylhydrazines.

Key words

MCPBA - sulfenylhydrazines - sulfonylhydrazines - oxidation - addition - azodicarboxylates - thiols - thiophenols

• References

• 1a Seow HA, Penketh PG, Shyam K, Rockwell S, Sartorelli AC. Proc. Natl. Acad. Sci. U.S.A. 2005; 102: 9282
• 1b Kamal A, Khan MN. A, Reddy KS, Rohini K. Bioorg. Med. Chem. 2007; 15: 1004
• 1c Penketh PG, Shyam K, Baumann RP, Remack JS, Brent TP, Sartorelli AC. Cancer Chemother. Pharmacol. 2004; 53: 279
• 1d Baumann RP, Seow HA, Shyam K, Penketh PG, Sartorelli AC. Oncol. Res. 2005; 15: 313
• 1e Powers JP, Piper DE, Li Y, Mayorga V, Anzola J, Chen JM. J. Med. Chem. 2006; 49: 1034
• 1f Baumann RP, Ishiguro KP, Penketh G, Shyam K, Zhu R, Sartorelli AC. Biochem. Pharmacol. 2011; 81: 1201
• 1g Al-Azzawi AM, Razzak MS. A. J. Pharm. Sci. 2011; 2: 124
• 1h Sondhi SM, Dinodia M, Kumar A. Bioorg. Med. Chem. 2006; 14: 4657
• 1i Ignat A, Zaharia V, Mogosan C, Palibroda N, Cristea C. Farmacia 2010; 58: 290
• 2a Taniguchi T, Idota A, Ishibashi H. Org. Biomol. Chem. 2011; 9: 3151
• 2b Li X, Xu X, Zhou C. Chem. Commun. 2012; 48: 12240
• 2c Liu B, Li J, Song F, You J. Chem. Eur. J. 2012; 18: 10830
• 2d Li X, Xu X, Tang Y. Org. Biomol. Chem. 2013; 11: 1739
• 2e Li X, Xu X, Hu P, Xiao X, Zhou C. J. Org. Chem. 2013; 78: 7343
• 3a Dodoff NI, Ozdemir U, Karacan N, Georgieva M, Konstantinov SM, Stefanova ME. Z. Naturforsch. 1999; 54: 1553
• 3b Grehn L, Lonn H, Ragnarsson U. Chem. Commun. 1997; 7: 1381
• 4a Nguyen B, Emmet EJ, Willis MC. J. Am. Chem. Soc. 2010; 132: 16372
• 4b Emmett AJ, Richards-Taylor CS, Nguyen B, Garcia-Rubia A, Hayter BR, Willis MC. Org. Biomol. Chem. 2012; 10: 4007
• 4c Richards-Taylor CS, Blackmore DC, Wills MC. Chem. Sci. 2014; 5: 222
• 4d Ye S, Wu J. Chem. Commun. 2012; 48: 7753
• 4e Ye S, Wu J. Chem. Commun. 2012; 48: 10037
• 4f Zheng D, An Y, Li Z, Wu J. Angew. Chem. Int. Ed. 2014; 53: 2451
• 5 Wang X, Xue L, Wang Z. Org. Lett. 2014; 16: 4056
• 6 Yang ZH, Xu W, Wu QY, Xu JX. J. Org. Chem. 2016; 81: 3051
• 7a Chan WY, Berthelette C. Tetrahedron Lett. 2002; 43: 4537
• 7b Wen JW, Wei W, Yang DS, Fan YF, Fu LL, Wang H. Synth. Commun. 2015; 45: 1574
• 8 Zhou BN, Xu JX. Org. Biomol. Chem. 2016; 14: 4918
• 9 Linke KH, Brandt W, Gohausen H. Chem. Ber. 1973; 106: 707
• 10a Mukaiyama T, Takahashi K. Tetrahedron Lett. 1968; 9: 5907
• 10b Gottschling D, Seliger H, Tarraso G, Piulats J, Eritja R. Bioconjugate Chem. 1998; 9: 831
• 10c Hummel G, Hindsgaul O. Angew. Chem. Int. Ed. 1999; 38: 1782
• 10d Far S, Melnyk O. Tetrahedron Lett. 2004; 45: 7163
• 10e Far S, Gouyette C, Melnyk O. Tetrahedron 2005; 61: 6138
• 10f Roychowdhury A, Illangkoon H, Hendrickson CL, Benner SA. Org. Lett. 2004; 6: 489
• 10g Cai JF, Li XX, Taylor JS. Org. Lett. 2005; 7: 751
• 10h Biel M, Deck P, Giannis A, Waldmann H. Chem. Eur. J. 2006; 12: 4121
• 10i Sato R, Kimura T. Acyclic Di- and Polysulfides, In Science of Synthesis . Vol. 39. Kambe N. Thieme; Stuttgart: 2007: 573
• 10j Rentero SP, Garibotti AV, Eritja R. Molecules 2010; 15: 5692
• 10k Bailey JJ, Bundle DR. Org. Biomol. Chem. 2014; 12: 2193
• 11 Fleming SA, Rawlins DB, Samano V, Robins MJ. J. Org. Chem. 1992; 57: 5968
• 12 Hao HX, Hu WH. Synlett 2007; 1314
• 13 Bahrami K, Khodaei MM, Yousefi BH, Arabi MS. Tetrahedron Lett. 2010; 51: 6939
• 14 Yu B, Liu AH, He LN, Li B, Diao ZF, Li YN. Green Chem. 2012; 14: 957
• 15a Masterson DS, Porter NA. J. Org. Chem. 2004; 69: 3693
• 15b Stensaas KL, McCarty BV, Touchette NM, Brock JB. Tetrahedron 2006; 62: 10683
• 16 Ruano JL. G, Parra A, Yuste F, Mastranzo VM. Synthesis 2008; 311