A New, Simple, and General Synthesis of N-Oxides of Iodopyridines and Iodoquinolines via the Diazotization–Iodination of Heterocyclic Amino N-Oxides in the Presence of p-Toluenesulfonic Acid in Water

Abstract

The diazotization of a series of N-oxides of aminopyridines and aminoquinolines under the action of sodium nitrite in the presence of KI and p-TsOH in water at room temperature leads to the formation of the corresponding N-oxides of iodopyridines and iodoquinolines in high yields. The method has a general character and can be used for the preparation of 3-, 2-, and 4- N-oxides of iodopyridines.

Key words

diazo compounds - pyridines - quinolines - halogenation - iodine

• References

• 1 Loones KT. J. Maes BU. W. Dommisse RA. Tetrahedron 2007; 63: 8954
• 2 Boganyi B. Kaman J. Tetrahedron 2013; 69: 9512
• 3 Duan X.-F. Ma Z.-Q. Zhang F. Zhang Z.-B. J. Org. Chem. 2009; 74: 939
• 4 Daab JC. Bracher F. Monatsh. Chem. 2003; 134: 573
• 5a Kasibhatla SR. Hong K. Biamonte MA. Busch DJ. Karjian PL. Sensintaffar GL. Kamal K. Lough LE. Brekken J. Lundgren K. Grecko R. Timony GA. Ran Y. Mansfield R. Fritz LC. Ulm E. Burrows FJ. Boehm MF. J. Med. Chem. 2007; 50: 2767
• 5b Finney K.-LN. A. Harnden AC. Rogers NJ. Senanayake PK. Blamire AM. O’Hogain D. Parker D. Chem. Eur. J. 2017; 23: 7976
• 5c Pavlik JW. Laohhasurayotin S. J. Heterocycl. Chem. 2007; 44: 1485

For example, see:
• 6a Yu L.-F. Zhang H.-K. Caldrone BJ. Eaton JB. Lukas RJ. Kozikowski AP. J. Med. Chem. 2014; 57: 8204
• 6b Liu Y. Yu H. Zhao L. Zhang H. Nucl. Med. Biol. 2013; 40: 126
• 6c Silpa L. Niepceron A. Laurent F. Brossier F. Penichon M. Enguehard-Gueiffier C. Abarbri M. Silvestre A. Petrignet J. Bioorg. Med. Chem. Lett. 2016; 26: 114
• 6d Veliks J. Tseng J.-C. Arias KI. Weisshar F. Linden A. Siegel JS. Chem. Sci. 2014; 5: 4317

See reviews:
• 7a Galli C. Chem. Rev. 1988; 88: 765
• 7b Sloan NL. Sutherland A. Synthesis 2016; 48: 2969
• 8a Penicaud V. Odobel F. Bujoli B. Tetrahedron Lett. 1998; 39: 3689
• 8b Sprecher M. Breslow R. Uziel O. Link TM. Org. Prep. Proced. Int. 1994; 26: 696
• 8c Klunder JM. Hoermann MA. Cywin CL. David E. Brickwood JR. Schwartz R. Barringer KJ. Pauletti D. Shih C.-K. Erickson DA. Sorge CL. Joseph DP. Hattox SE. Adams J. Grob PM. J. Med. Chem. 1998; 41: 2960
• 8d Kennedy-Smith JJ. Arora N. Billedeau JR. Fretland J. Hang JQ. Heilek GM. Harris SF. Hirschfeld D. Javanbakht H. Li Y. Liang W. Roetz R. Smith M. Su G. Suh JM. Villasenor AG. Wu J. Yasuda D. Klumpp K. Sweeney ZK. Med. Chem. Commun. 2010; 1: 79
• 8e Delgado O. Muller HM. Bach T. Chem. Eur. J. 2008; 14: 2322
• 8f Letessier J. Detert H. Synthesis 2012; 44: 290
• 8g Billaud EM. F. Maisonial-Besset A. Rbah-Vidal L. Vidal A. Besse S. Bequignat J.-B. Decombat C. Degoul F. Audin L. Deloye J.-B. Dolle F. Kuhnast B. Madelmont J.-C. Tarrit S. Galmier M.-J. Borel M. Auzeloux P. Miot-Noirault E. Chezal J.-M. Eur. J. Med. Chem. 2015; 92: 818
• 8h Krasnokutskaya EA. Semenischeva NI. Filimonov VD. Knochel P. Synthesis 2007; 81
• 9a Bracher F. Daab J. Eur. J. Org. Chem. 2002; 2288
• 9b Verdelet T. Mercey G. Correa N. Jean L. Renard P.-J. Tetrahedron 2011; 67: 8757
• 9c Sapountzis I. Dube H. Lewis R. Gommermann N. Knochel P. J. Org. Chem. 2005; 70: 2445
• 9d Baik W. Luan W. Lee HJ. Yoon CH. Koo S. Kim BH. Can. J. Chem. 2005; 83: 213
• 9e Coudret C. Synth. Commun. 1996; 26: 3543
• 10 Loones KT. J. Maes BU. W. Herrebout WA. Dommisse RA. Lemiere GL. F. Van der Veken B. Tetrahedron 2007; 63: 3818
• 11a Filimonov VD. Trusova ME. Postnikov PS. Krasnokutskaya EA. Lee YM. Hwang HY. Kim H. Chi K.-W. Org. Lett. 2008; 10: 3961
• 11b Filimonov VD. Semenischeva NI. Krasnokutskaya EA. Tretyakov AN. Hwang HY. Chi K.-W. Synthesis 2008; 185
• 11c Gorlushko DA. Filimonov VD. Krasnokutskaya EA. Semenischeva NI. Go BS. Hwang HY. Chi K-W. Tetrahedron Lett. 2008; 49: 1080
• 11d Moon ME. Choi Y. Lee YM. Vajpayee V. Trusova ME. Filimonov VD. Chi K.-W. Tetrahedron Lett. 2010; 51: 6769
• 11e Lee YM. Moon ME. Vajpayee V. Filimonov VD. Chi K.-W. Tetrahedron 2010; 66: 7418
• 11f Trusova ME. Krasnokutskaya EA. Postnikov PS. Choi Y. Chi K.-W. Filimonov VD. Synthesis 2011; 2154
• 11g Vajpayee V. Moon ME. Lee S. Ravikumar S. Kim H. Ahn B. Choi S. Hong SH. Chi K-W. Tetrahedron 2013; 69: 3511
• 11h Sloan NL. Luthra SK. McRobbie G. Pimlott SL. Sutherland A. Chem. Commun. 2017; 53: 11008
• 12a Tretyakov AN. Krasnokutskaya EA. Gorlushko DA. Ogorodnikov VD. Filimonov VD. Tetrahedron Lett. 2011; 52: 85
• 12b Krasnokutskaya EA. Kassanova AZ. Estaeva MT. Filimonov VD. Tetrahedron Lett. 2014; 55: 3771
• 12c Kassanova AZ. Krasnokutskaya EA. Beisembai PS. Filimonov VD. Synthesis 2016; 48: 256
• 13a Kondo S. Funakoshi K. Saeki S. Hamana M. Chem. Pharm. Bull. 1986; 34: 7
• 13b Katritzky AR. J. Chem. Soc. 1957; 88: 191
• 14 Suzuki Y. Yakugaku Zasshi 1961; 81: 1204 ; Chem. Abstr. 1962, 56, 3445d
• 15 Kozhevnikova AN. Shvatsberg MS. Kotlyarevskii IL.  Bull. Acad. Sci. USSR, Div. Chem. Sci. 1973; 5: 1132
• 16 Puszko A. Magn. Reson. Chem. 1992; 30: 271
• 17 Ghersetti S. Maccagnani AM. Montanari F. J. Heterocycl. Chem. 1969; 6: 859
• 18 Jeong J. Lee D. Chang S. Chem. Commun. 2015; 51: 7035
• 19 Hwang H. Kim J. Jeong J. Chang S. J. Am. Chem. Soc. 2014; 30: 10770
• 20 Leslie WD. Synth. Commun. 1977; 7: 509
• 21 Song JJ. Yee NK. J. Org. Chem. 2001; 66: 605
• 22 Schlosser M. Cottet F. Eur. J. Org. Chem. 2002; 4181
• 23 Bartucci MA. Ciszek JW. J. Org. Chem. 2014; 79: 5586