Synthesis 2018; 50(06): 1368-1372
DOI: 10.1055/s-0036-1591738
paper
© Georg Thieme Verlag Stuttgart · New York

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
The research was funded by the Tomsk Polytechnic University Competitiveness Enhancement Program grant, Project Number VIU-TOVPM-316/2017. EAK thanks RFBR grant 17-03-01097.
Further Information

Publication History

Received: 10 October 2017

Accepted after revision: 15 November 2017

Publication Date:
13 December 2017 (online)


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.

Supporting Information

 
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