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

doi:10.1055/s-0036-1591738

Synthesis, Table of Contents

Synthesis 2018; 50(06): 1368-1372
DOI: 10.1055/s-0036-1591738

paper

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*

Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 634050 Tomsk, Russian Federation Email: eak@tpu.ru

,

Alexey A. Chudinov

Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 634050 Tomsk, Russian Federation Email: eak@tpu.ru

,

Victor D. Filimonov

Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 634050 Tomsk, Russian Federation Email: eak@tpu.ru

› Author Affiliations

Abstract

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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

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References

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