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Direct Amination of Nitroquinoline Derivatives via Nucleophilic Displacement of Aromatic Hydrogen.

ABSTRACT: The vicarious nucleophilic substitution of hydrogen (VNS) reaction in electron-deficient nitroquinolines was studied. Properties of all new products have been characterized by several techniques: MS, HRMS, FTIR, GC-MS, electronic absorption spectroscopy, and multinuclear NMR. The structures of 4-chloro-8-nitroquinoline, 8-(tert-butyl)-2-methyl-5-nitroquinoline, 9-(8-nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one were determined by single-crystal X-ray diffraction measurements. The 9-(8-nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one illustrate the nitro/nitroso conversion within VNS reaction. Additionally, 9-(8-isopropyl-2-((8-isopropyl-2-methyl-5-nitroquinolin-6-yl)methyl)-5-nitrosoquinolin-6-yl)-9H-carbazole is presented as a double VNS product. It is postulated that the potassium counterion interacts with the oxygen on the nitro group, which could influence nucleophile attack in that way.

SUBMITTER: Wantulok J 

PROVIDER: S-EPMC8036465 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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Direct Amination of Nitroquinoline Derivatives via Nucleophilic Displacement of Aromatic Hydrogen.

Wantulok Jakub J   Swoboda Daniel D   Swoboda Daniel D   Nycz Jacek E JE   Książek Maria M   Kusz Joachim J   Małecki Jan Grzegorz JG   Kubíček Vladimír V  

Molecules (Basel, Switzerland) 20210325 7

The vicarious nucleophilic substitution of hydrogen (VNS) reaction in electron-deficient nitroquinolines was studied. Properties of all new products have been characterized by several techniques: MS, HRMS, FTIR, GC-MS, electronic absorption spectroscopy, and multinuclear NMR. The structures of 4-chloro-8-nitroquinoline, 8-(<i>tert</i>-butyl)-2-methyl-5-nitroquinoline, 9-(8-nitroquinolin-7-yl)-9<i>H</i>-carbazole and (<i>Z</i>)-7-(9<i>H</i>-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8<i>H</i>)-one  ...[more]

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