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

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

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 anhydr...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2022-11, Vol.27 (22), p.7862
Hauptverfasser: Avakyan, Elena K, Borovleva, Anastasia A, Pobedinskaya, Diana Yu, Demidov, Oleg P, Ermolenko, Artem P, Larin, Alexander N, Borovlev, Ivan V
Format: Artikel
Sprache:eng
Schlagworte:
5-nitroisoquinoline
Alkaloids
Amides
heterocycles
Hydrogen bonds
Isoquinolines
metal-free C–N bond formation
Nitroquinolines
oxidative SNH amidation
redox process
SNH methodology
Urea
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Beschreibung
Zusammenfassung: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27227862