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

Elena A. Krasnokutskaya, Alexey A. Chudinov, Victor D. Filimonov

The Kizhner Research Center

Research output: Contribution to journal › Article

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.

Original language	English
Pages (from-to)	1368-1372
Number of pages	5
Journal	Synthesis (Germany)
Volume	50
Issue number	6
DOIs	https://doi.org/10.1055/s-0036-1591738
Publication status	Accepted/In press - 13 Dec 2017

Fingerprint

Oxides

Acids

Water

Aminoquinolines

Aminopyridines

Sodium Nitrite

Sodium

4-toluenesulfonic acid

Temperature

Keywords

diazo compounds
halogenation
iodine
pyridines
quinolines

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Cite this

Krasnokutskaya, E. A., Chudinov, A. A., & Filimonov, V. D. (Accepted/In press). 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. Synthesis (Germany), 50(6), 1368-1372. https://doi.org/10.1055/s-0036-1591738

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. / Krasnokutskaya, Elena A.; Chudinov, Alexey A.; Filimonov, Victor D.

In: Synthesis (Germany), Vol. 50, No. 6, 13.12.2017, p. 1368-1372.

Research output: Contribution to journal › Article

Krasnokutskaya, EA, Chudinov, AA & Filimonov, VD 2017, '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', Synthesis (Germany), vol. 50, no. 6, pp. 1368-1372. https://doi.org/10.1055/s-0036-1591738

Krasnokutskaya EA, Chudinov AA, Filimonov VD. 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. Synthesis (Germany). 2017 Dec 13;50(6):1368-1372. https://doi.org/10.1055/s-0036-1591738

Krasnokutskaya, Elena A. ; Chudinov, Alexey A. ; Filimonov, Victor D. / 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. In: Synthesis (Germany). 2017 ; Vol. 50, No. 6. pp. 1368-1372.

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Access to Document

10.1055/s-0036-1591738