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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)1368-1372
Number of pages5
JournalSynthesis (Germany)
Volume50
Issue number6
DOIs
Publication statusAccepted/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

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title = "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.",
keywords = "diazo compounds, halogenation, iodine, pyridines, quinolines",
author = "Krasnokutskaya, {Elena A.} and Chudinov, {Alexey A.} and Filimonov, {Victor D.}",
year = "2017",
month = "12",
day = "13",
doi = "10.1055/s-0036-1591738",
language = "English",
volume = "50",
pages = "1368--1372",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "6",

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TY - JOUR

T1 - 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

AU - Krasnokutskaya, Elena A.

AU - Chudinov, Alexey A.

AU - Filimonov, Victor D.

PY - 2017/12/13

Y1 - 2017/12/13

N2 - 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.

AB - 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.

KW - diazo compounds

KW - halogenation

KW - iodine

KW - pyridines

KW - quinolines

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DO - 10.1055/s-0036-1591738

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JO - Synthesis

JF - Synthesis

SN - 0039-7881

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