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.

[1]  Sukbok Chang,et al.  Copper-catalyzed oxygen atom transfer of N-oxides leading to a facile deoxygenation procedure applicable to both heterocyclic and amine N-oxides. , 2015, Chemical communications.

[2]  J. Ciszek,et al.  Substituent parameters impacting isomer composition and optical properties of dihydroindolizine molecular switches. , 2014, The Journal of organic chemistry.

[3]  J. Kámán,et al.  A concise synthesis of indoloquinoline skeletons applying two consecutive Pd-catalyzed reactions , 2013 .

[4]  Fang Zhang,et al.  Magnesiation of pyridine N-oxides via iodine or bromine-magnesium exchange: a useful tool for functionalizing pyridine N-oxides. , 2009, The Journal of organic chemistry.

[5]  R. Dommisse,et al.  Synthesis of pyrido[2′,1′:2,3]imidazo[4,5-b]quinoline and pyrido[1′,2′:1,2]imidazo[4,5-b]quinoline and their benzo and aza analogs via tandem catalysis , 2007 .

[6]  R. Dommisse,et al.  Examination of the mechanism of the intramolecular amination of N-(3 -bromopyridin -2 -yl )azaheteroarylamines and N-(2-chloropyridin-3-yl)azaheteroarylamines : a Pd-catalyzed amination and/or a base-assisted nucleophilic aromatic substitution? , 2007 .

[7]  F. Bracher,et al.  Total Syntheses of the Alkaloids Ipalbidinium and Clathryimine B , 2003 .

[8]  N. Yee,et al.  A concise synthesis of fusaric acid and (S)-(+)-fusarinolic acid. , 2001, The Journal of organic chemistry.

[9]  A. Puszko.  Carbon‐13 nuclear magnetic resonance. Study of 2‐halopicolines, their N‐oxides and 2‐halo‐4‐nitropicoline N‐oxides , 1992 .

[10]  Yasuyuki Suzuki.  Synthesis of 4-Substituted Pyridines and their Homologs , 1961 .