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Microwave-assisted rapid synthesis of arylazoxy sulfides

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Abstract

An efficient, fast, and straightforward procedure for the synthesis of arylazoxy sulfides can be achieved by coupling reaction between aryl nitrasocompounds and tribenzenesulphenamide under microwave irradiation. Using the present method, different kinds of aryl nitrasocompounds containing various dioxolane rings and various tribenzenesulphenamide derivatives were rapidly converted to the corresponding arylazoxy sulfides in good yield and short reaction time. The use of non-toxic solvent, simple and clean work-up, short reaction times and good yields are the advantages of this method.

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References

  1. Roglans A, Pla-Quintana A and Moreno-Mañas M 2006 Diazonium salts as substrates in palladium-catalyzed cross-coupling reactions Chem. Rev. 106 4622

    Article  CAS  Google Scholar 

  2. Wood W W, Kremp G, Petry T and Simon W E J 1999 New and improved syntheses of arylazoxycyanides Synth. Commun. 29 619

    Article  CAS  Google Scholar 

  3. Cygler M, Przybylska M and Elofson R M 1982 The crystal structure of benzenediazoniumtetrafluoroborate Can. J. Chem. 60 2852

    Article  CAS  Google Scholar 

  4. Martin N J A and List B 2006 Highly enantioselective transfer hydrogenation of α, β-unsaturated ketones J. Am. Chem. Soc. 128 13368

    Article  CAS  Google Scholar 

  5. Tuttle J B, Ouellet, S G and MacMillan, D W C 2006 Organocatalytic transfer hydrogenation of cyclic enones J. Am. Chem. Soc. 128 12662

    Article  CAS  Google Scholar 

  6. Galli C 1988 Radical reactions of arenediazonium ions: an easy entry into the chemistry of the aryl radical Chem. Rev. 88 765

    Article  CAS  Google Scholar 

  7. Barbero M, Crisma M, Degani I, Fochi R and Perracino P 1998 New dry arenediazonium salts, stabilized to an exceptionally high degree by the anion of o-benzenedisulfonimide Synthesis 8 1171

    Article  Google Scholar 

  8. Barbero M, Degani I, Dugheroand S and Fochi R 1999 Halodediazoniations of dry arenediazonium o-benzenedisulfonimides in the presence or absence of an electron transfer catalyst J. Org. Chem. 64 3448

    Article  CAS  Google Scholar 

  9. Lythgoe and Riggs N V 1949 Macrozamin. Part I. The identity of the carbohydrate component J. Chem. Soc. 2716

  10. Langley B W, Lythgoe B and Riggs N V 1951 Macrozamin. Part II. The aliphatic azoxy structure of the aglycone part J. Chem. Soc. 2309

  11. Korsch B and Riggs N V 1964 Proton magnetic resonance spectra of aliphatic azoxy compounds and the structure of cycasin Tetrahedron Lett. 5 523

    Article  Google Scholar 

  12. Matsumoto H, Nagahama T and Larson H O 1965 Studies on methylazoxy: the aglycone of cycasin Biochem. J. 95 13c

  13. Stevens C L, Gillis B T, French J C, Haskell T H and Ameer J 1956 Elaiomycin—an over view J. Chem. Soc. 78 3229

    Article  CAS  Google Scholar 

  14. Wood W W, Kremp G, Petry T and Simon W E J 1999 New and improved syntheses of arylazoxy cyanides Synth. Commun. 29 619

    Article  CAS  Google Scholar 

  15. Gray A C G, Kremp G, Naisby T W, Simon T P W, Wilkin J and Wood W W 2002 Calvatic acid and its analogues as agricultural fungicides Synth. Chem. Agrochem. 27 292

    Google Scholar 

  16. Xu B and Zhu S 1998 A convenient route to N-perfluoroalkanesulfonyl, N′-phenyldiazene N′-oxide J. Fluor. Chem. 90 59

    Article  Google Scholar 

  17. Zarei A, Khazdooz L, Hajipour A R and Aghaei H 2011 Fast efficient and convenient method for the preparation of arylazo sulfides using aryl diazonium silica sulfates under mild and solvent-free conditions Dyes Pigments 91 44

    Article  CAS  Google Scholar 

  18. Lian C, Yue G, Mao J, Liu D, Ding Y, Liu Z, Qiu D, Zhao X, Lu K, Fagnoni M and Protti S 2019 Visible-light-driven synthesis of arylstannanes from arylazo sulfones Org. Lett. 21 5187

    Article  CAS  Google Scholar 

  19. Kamigata N, Satoh M, Yoshida M, Nakamura Y, Kikuchi K and Ikemoto I 1991 Novel reaction of arylazo aryl and arylazoxy aryl sulfones Phosphorus Sulfur Silicon Relat. Elem. 69 129–136

    Article  Google Scholar 

  20. Kamigata N, Satoh M and Yoshida M 1991 A novel tandum arylsulfonylation and cyclization of arylazoxy aryl sulfones J. Organomet. Chem. 401 C26–C29

    Article  CAS  Google Scholar 

  21. Barton D H R, Blair I A, Magnus P D and Norris R K 1973 The Chemistry of trisulphenamides part-I J. Chem. Soc. Perkin Trans. 1 1031

    Article  Google Scholar 

  22. Almog J, Barton D H R, Magnus P D and Norris R K 1974 The chemistry of trisulphenamides part-III J. Chem. Soc. Perkin Trans. 1 853

    Article  Google Scholar 

Download references

Acknowledgment

The authors are grateful to GVK Biosciences Pvt Ltd (Hyderabad, India) and Koneru Lakshmaiah Education Foundation (KLEF), Green Fields, Vaddeswaram, Guntur for their support.

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Correspondence to I V KASIVISWANATH.

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GANDIKOTA, N.M., MENDU, N., KASIVISWANATH, I.V. et al. Microwave-assisted rapid synthesis of arylazoxy sulfides. J Chem Sci 132, 77 (2020). https://doi.org/10.1007/s12039-020-01782-5

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  • DOI: https://doi.org/10.1007/s12039-020-01782-5

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