SNH Amidation of 5-Nitroisoquinoline: Access to Nitro- and Nitroso Derivatives of Amides and Ureas on the Basis of Isoquinoline

Elena K Avakyan; Anastasia A Borovleva; Diana Yu Pobedinskaya; Oleg P Demidov; Artem P Ermolenko; Alexander N Larin; Ivan V Borovlev

doi:10.3390/molecules27227862

SNH Amidation of 5-Nitroisoquinoline: Access to Nitro- and Nitroso Derivatives of Amides and Ureas on the Basis of Isoquinoline

Molecules. 2022 Nov 14;27(22):7862. doi: 10.3390/molecules27227862.

Authors

Elena K Avakyan¹, Anastasia A Borovleva¹, Diana Yu Pobedinskaya¹, Oleg P Demidov¹, Artem P Ermolenko¹, Alexander N Larin¹, Ivan V Borovlev¹

Affiliation

¹ Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, Russia.

Abstract

For the first time, amides and ureas based on both 5-nitroisoquinoline and 5-nitrosoisoquinoline were obtained by direct nucleophilic substitution of hydrogen in the 5-nitroisoquinoline molecule. In the case of urea and monosubstituted ureas, only 5-nitrosoisoquinoline-6-amine is formed under anhydrous conditions.

Keywords: 5-nitroisoquinoline; SNH dialkylcarbamoylamination; SNH methodology; heterocycles; metal-free C–N bond formation; oxidative SNH amidation; redox process; regioselectivity.

MeSH terms

Amides
Isoquinolines
Nitroquinolines*
Urea*

Substances

Urea
Amides
5-nitroquinoline
Nitroquinolines
Isoquinolines

Grants and funding

The authors express their gratitude to the North Caucasian Federal University for financial support in the framework of the project to support the projects of scientific groups and individual scientists.