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Efficient iron(III) porphyrins-catalyzed oxidation of guanidoximes to cyanamides in ionic liquids

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Abstract

Water soluble iron(III) porphyrins immobilized in imidazolium ionic liquids serve as an effective catalyst for the H2O2 mediated oxidation of guanidoximes to selectively give corresponding cyanamides in good yields. The use of ionic liquid with non-coordinating counter anion PF6 affords the product in high yield by facilitating the formation of anionic iron peroxo intermediate.

The selective oxidation of guanidoximes to corresponding cyanamides has been achieved by H2O2 catalyzed by water-soluble iron(III) porphyrins immobilized in imidazolium ionic liquids. The non-coordinating ionic liquid [bmim][PF6] facilitates the formation of anionic iron peroxo intermediate and thereby gives products in highest yield.

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References

  1. Renodon-Cornière A, Dijols S, Perollier C, Lefevre-Groboillot D, Boucher J L, Attias R, Sari M A, Stuehr D and Mansuy D 2002 J. Med. Chem. 45 944

  2. Renodon-Corniere A, Boucher J L, Dijols S, Stuehr D J and Mansuy D 1999 Biochem. 38 4663

  3. Clague M J, Wishnok J S and Marletta M A 1997 Biochem. 36 14465

  4. Jousserandot A, Boucher J L, Henry Y, Niklaus B, Clement B and Mansuy D 1998 Biochem. 37 17179

  5. Jousserandot A, Boucher J L, Desseaux C, Delaforge M and Mansuy D 1995 Bioorg. Med. Chem. Lett. 5 423

  6. Sennequier N, Boucher J L, Battioni P and Mansuy D 1995 Tetrahedron Lett. 36 6059

  7. Ricoux R, Boucher J L, Mandon D, Frapart Y M, Henry Y, Mansuy D and Mahy J P 2003 Eur. J. Biochem. 270 47

  8. Keseru G M, Balogh G T and Karancsi T 2000 Bioorg. Med. Chem. Lett. 10 1775

  9. Goff S V L, Boucher J L and Mansuy D 2000 Chemistry 785

  10. Fukuto J, Wallace G C, Hszieh R and Chaudhrui G 1992 Biochem. Pharmacol. 43 607

  11. Jain N, Kumar A and Chauhan S M S 2005 Tetrahedron Lett. 46 2599

  12. Zhou X T, Yuan Q L and Ji H B 2010 Tetrahedron Lett. 51 613

  13. Habibi D, Faraji A R Arshadi M, Veisi H and Gil A 2014 J. Mol. Catal. A: Chem. 382 41

  14. Hart-Davis J, Battioni P, Boucher J L and Mansuy D 1998 J. Am. Chem. Soc. 120 12524

  15. Liao R Z and Thiel W 2012 J. Phys. Chem. B 116 9396

  16. Fatiadi A J 1983 In Preparation and synthetic applications of cyano compounds S Patai and Z Rappaport (Eds.) (New York: Wiley)

  17. Sheldon R A 1994 In Metalloporphyrins in catalytic oxidations (New York: M. Dekker Inc.)

  18. Sowmiah S, Cheng C I and Chu Y H 2012 Curr. Org. Syn. 9 74

  19. Kumari P, Sinha N, Chauhan P and Chauhan S M S 2011 Curr. Org. Syn. 8 393

  20. Singh P P, Ambika, Chauhan S M S 2012 New J. Chem. 36 650

  21. Ahmad S, Yadav K K and Chauhan S M S 2012 Curr. Org. Chem. 16 2989

  22. Singhal A and Chauhan S M S 2012 Catal. Commun. 25 28.207

  23. Stefan L, Xu H J, Gros C P, Denat F and Monchaud D 2011 Chem. - A Eur. J. 17 10857

  24. Bailey D M and De Grazia G 1973 J. Med. Chem. 16 151

  25. (a) Nath J, Patel B K, Jamir L, Sinha U B and Satyanarayana K V 2009 Green Chem. 11 1503; (b) Ghosh H, Yella R, Ali A R, Sahoo S K and Patel B K 2009 Tetrahedron Lett. 50 2407

  26. Lin C-C, Hsieh T-H, Liao Z-Y, Chang C-W, Shih Y-C, Yeh W-H and Chien T-C 2014 Org. Lett. 16 892

  27. Lee J W, Shin J Y, Chun Y S, Jang H B, Song C E and Lee S 2010 Acc. Chem. Res. 43 985

  28. Hallett J P and Welton T 2011 Chem. Rev. 111 3508

  29. Maia A 2011 Mini-Reviews in Organic Chemistry 8 178

  30. Kumari P, Nagpal R and Chauhan S M S 2012 Catal. Commun. 29 15

  31. Meunier B, De Visser S P and Shaik S 2004 Chem. Rev. 104 3947

  32. Nam W, Lim M H, Lee H J and Kim C 2000 J. Am. Chem. Soc. 122 6641

  33. Jameson L P, Kimball J D, Gryczynski Z, Balaz M and Dzyuba S V 2013 RSC Adv. 3 18300

  34. Choi D S, Kim D H, Shin U S, Deshmukh R R, Lee S and Song C E 2007 Chem. Commun. 33 3467

  35. Compton D L, Laszlo J L and Joseph A 2002 J. Electroanal. Chem. 520 71

  36. Stephenson N A and Bell A T 2007 Inorg. Chem. 46 2278

  37. Bell S R and Groves J T 2009 J. Am. Chem. Soc. 131 9640

  38. Fukuto J M, Stuehr D J, Feldman P L, Bova M P and Wong P 1993 J. Med. Chem. 36 2666

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Acknowledgements

The authors are grateful to the Council of Scientific and Industrial Research, New Delhi and University of Delhi for financial assistance.

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KUMARI, P., NAGPAL, R., CHAUHAN, P. et al. Efficient iron(III) porphyrins-catalyzed oxidation of guanidoximes to cyanamides in ionic liquids. J Chem Sci 127, 13–18 (2015). https://doi.org/10.1007/s12039-014-0751-4

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