Synthesis 2017; 49(07): 1648-1654
DOI: 10.1055/s-0036-1588370
paper
© Georg Thieme Verlag Stuttgart · New York

Highly Regioselective Iodination of N-Phenylureas with Iodine/Trichloroisocyanuric Acid

Carlos M. Sanabria
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68545, 21945-970, Rio de Janeiro, Brazil   Email: luciasequeira@yahoo.com.br   Email: mmattos@iq.ufrj.br
,
Mariana T. do Casal
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68545, 21945-970, Rio de Janeiro, Brazil   Email: luciasequeira@yahoo.com.br   Email: mmattos@iq.ufrj.br
,
Raphael B. A. de Souza
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68545, 21945-970, Rio de Janeiro, Brazil   Email: luciasequeira@yahoo.com.br   Email: mmattos@iq.ufrj.br
,
Lúcia C. S. de Aguiar*
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68545, 21945-970, Rio de Janeiro, Brazil   Email: luciasequeira@yahoo.com.br   Email: mmattos@iq.ufrj.br
,
Marcio C. S. de Mattos*
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68545, 21945-970, Rio de Janeiro, Brazil   Email: luciasequeira@yahoo.com.br   Email: mmattos@iq.ufrj.br
› Author Affiliations
Further Information

Publication History

Received: 05 October 2016

Accepted after revision: 14 November 2016

Publication Date:
19 December 2016 (online)


Dedicated to the memory of Prof. José Barluenga

Abstract

An efficient regioselective iodination of N-phenylureas was developed using iodine/trichloroisocyanuric acid in acetonitrile at room temperature. This protocol proved to be effective on a broad range of substituted N-phenylureas, forming the p-iodinated compounds in 65–96% yield under mild and neutral conditions.

Supporting Information

 
  • References

    • 1a Omokawa H, Ryoo JH, Kashiwabara S. Biosci., Biotechnol., Biochem. 1999; 63: 349
    • 1b Zhao B, Baston D, Hammock B, Denison MS. J. Biochem. Mol. Toxicol. 2006; 20: 103
  • 2 Nitschke C, Scherr G In Ullmann’s Encyclopedia of Industrial Chemistry . Vol. 38. Wiley–VCH; Weinhem: 2010
    • 3a Kim J, Davis R, Zentel R. J. Colloid Interface Sci. 2011; 359: 428
    • 3b Kim J, Schollmeyer D, Brehmer M, Zentel R. J. Colloid Interface Sci. 2011; 357: 428
    • 5a Pavia M, Lobbestael S, Taylor C, Hershenson F, Miskell D. J. Med. Chem. 1990; 33: 854
    • 5b Nava-Zuazo C, Estrada-Soto S, Guerrero-Álvarez J, León-Rivera I, Molina-Salinas G, Said-Fernández S, Chan-Bacab M, Cedillo-Rivera R, Moo-Puc R, Mirón-López G, Navarrete-Vazquez G. Bioorg. Med. Chem. 2010; 18: 6398
    • 5c Zheng Q.-Z, Cheng K, Zhang X.-M, Liu K, Jiao Q.-C, Zhu H.-L. Eur. J. Med. Chem. 2010; 45: 3207
    • 5d Pacchiano F, Carta F, Vullo D, Scozzafava A, Supuran C. Bioorg. Med. Chem. Lett. 2011; 21: 102
    • 5e Leban J, Pegoraro S, Dormeyer M, Lanzer M, Aschenbrenner A, Kramer B. Bioorg. Med. Chem. Lett. 2004; 14: 1979
    • 5f Zhang M, Yang X.-Y, Tang W, Groeneveld T, He P.-L, Zhu F.-H, Li J, Lu W, Blom A, Zuo J.-P, Nan F.-J. ACS Med. Chem. Lett. 2012; 3: 317
    • 5g Kurt B, Gazioglu I, Basile L, Sonmez F, Ginex T, Kucukislamoglu M, Guccione S. Eur. J. Med. Chem. 2015; 102: 80
    • 5h Perveen S, Fatima N, Khan MA, Afza N, Voelter W. Med. Chem. Res. 2012; 21: 2709
  • 6 Khan KM, Saeed S, Ali M, Gohar M, Zahid J, Khan A, Perveen S, Choudhary MI. Bioorg. Med. Chem. 2009; 17: 2447
  • 7 Darko AK, Curran FC, Copin C, McElwee-White L. Tetrahedron 2011; 67: 3976
    • 8a Luo W, Xia M.-Y, Ikejima T, Li L.-H, Guo C. Med. Chem. Res. 2013; 22: 3170
    • 8b Li H.-Q, Lv P.-C, Yan T, Zhu H.-L. Anticancer Agents Med. Chem. 2009; 9: 471
    • 8c Cainap C, Qin S, Huang W.-T, Chung IJ, Pan H, Cheng Y, Kudo M, Kang Y.-K, Chen P.-J, Toh H.-C, Gorbunova V, Eskens F, Qian J, McKee MD, Ricker JL, Carlson DM, El-Nowiem S. J. Clin. Oncol. 2015; 33: 172
    • 8d Motzer RJ, Nosov D, Eisen T, Bondarenko I, Lesovoy V, Lipatov O, Tomczak P, Lyulko O, Alyasova A, Harza M, Kogan M, Alekseev B, Sternberg C, Szczylik C, Cella D, Ivanescu C, Krivoshib A, Strahs A, Esteves B, Berkenblity A, Hutson TE. J. Clin. Oncol. 2013; 31: 3791
    • 9a Fortin S, Moreau E, Lacroix J, Côté M.-F, Petitclerc E, Gaudreault R. Eur. J. Med. Chem. 2010; 45: 2928
    • 9b Fortin J, Lacroix J, Desjardins M, Patenaude A, Petitclerc E, Gaudreault R. Bioorg. Med. Chem. 2007; 15: 4456
    • 9c Mounetou E, Miot-Noirault E, Gaudreault R, Madelmont JC. Invest. New Drugs 2010; 28: 124
    • 9d Trzeciakiewicz A, Fortin S, Moreau E, Gaudreault R, Lacroix J, Chambon C, Communal Y, Chezal J.-M, Miot-Noirault E, Bouchon B, Degoul F. Biochem. Pharmacol. 2011; 81: 1116
  • 10 Viana GM, Aguiar LC. S, Ferrão J, Simas AB. C, Vasconcelos MG. Tetrahedron Lett. 2013; 54: 936
  • 11 Senra JD, Viana GM, Malta LF, Simas AB. C, Aguiar LC. S. ChemCatChem 2016; 8: 192
    • 12a Zhan Y, Zhang H, Li J, Zhang Y, Zhang J, He L. J. Cell. Mol. Med. 2015; 19: 1614
    • 12b Wang C, Dong J, Zhang Y, Wang F, Gao H, Li P, Wang S, Zhang J. Med. Chem. Commun. 2013; 4: 1434
    • 13a Decker M, Si Y.-G, Knapp BI, Bidlack JM, Neumeyer JL. J. Med. Chem. 2010; 53: 402
    • 13b DeVries VG, Bloom JD, Dutia MD, Katocs AS, Largis EE. J. Med. Chem. 1989; 32: 2318
  • 14 Chutia R, Das G. Dalton Trans. 2014; 43: 15628
    • 15a Mendonça GF, de Mattos MC. S. Curr. Org. Synth. 2013; 10: 820
    • 15b de Almeida LS, Esteves PM, de Mattos MC. S. Curr. Green Chem. 2014; 1: 94
    • 15c Ribeiro RS, Esteves PM, de Mattos MC. S. J. Braz. Chem. Soc. 2008; 19: 1239
    • 15d Mendonça GF, de Mattos MC. S. Quim. Nova 2008; 31: 798
    • 15e de Almeida LS, Esteves PM, de Mattos MC. S. Synlett 2007; 1687
    • 15f de Almeida LS, Esteves PM, de Mattos MC. S. Synthesis 2006; 221
    • 15g Ribeiro RS, Esteves PM, de Mattos MC. S. J. Braz. Chem. Soc. 2012; 23: 228
    • 15h Mendonça GF, de Almeida LS, de Mattos MC. S, Esteves PM, Ribeiro RS. Curr. Org. Synth. 2015; 12: 603
    • 15i Lied F, Lerchen A, Knecht T, Mück-Lichtenfeld C, Glorious F. ACS Catal. 2016; 6: 7839
    • 15j Mishra AK, Nagarajaiah H, Moorthy JN. Eur. J. Org. Chem. 2015; 2733
    • 15k Maraš N, Kočevar M. Monatsh. Chem. 2015; 146: 697
  • 16 Tozetti SD. F, de Almeida LS, Esteves PM, de Mattos MC. S. J. Braz. Chem. Soc. 2007; 18: 675
    • 17a Akhlaghinia B, Rahmani M. Turk. J. Chem. 2009; 33: 67
    • 17b Akhlaghinia B, Rahmani M. J. Braz. Chem. Soc. 2010; 21: 3
  • 18 Casal MT, de Mattos MC. S. 36th Meeting of the Brazilian Chemical Society . Aguas de Lindoia; Brazil: 2013. Abstract ORG-35

    • Recent examples:
    • 19a de Andrade VC. S, de Mattos MC. S. Synthesis 2016; 48: 1381
    • 19b Sindra H, de Mattos MC. S. J. Braz. Chem. Soc. 2016; 27: 1129
    • 19c de Almeida LS, Esteves PM, de Mattos MC. S. Tetrahedron Lett. 2015; 56: 6843
    • 19d de Andrade VC. S, de Mattos MC. S. J. Braz. Chem. Soc. 2014; 25: 975
  • 20 Costa MV, Aguiar LC. S, Malta LF. B, Viana GM, Costa BB. S. Tetrahedron Lett. 2016; 57: 1585
  • 21 Stavber S, Jereb M, Zupan M. Synthesis 2008; 1487
    • 22a Mendonça GF, Senra MF, Esteves PM, de Mattos MC. S. Appl. Catal. A 2011; 401: 176
    • 22b de Almeida LS, Esteves PM, de Mattos MC. S. Tetrahedron Lett. 2009; 50: 3001
    • 22c da Ribeiro RS, Esteves PM, de Mattos MC. S. Synthesis 2011; 739
    • 22d de Almeida LS, de Mattos MC. S, Esteves PM. Synlett 2013; 24: 603
  • 23 Sah PP. T, Wang Y.-K. Recl. Trav. Chim. Pays-Bas 1940; 59: 364