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Synthesis of 4-nitro-γ-carbolines by Graebe–Ullmann reaction

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Chemistry of Heterocyclic Compounds Aims and scope

Graebe–Ullmann reaction was used to synthesize 3-aryl(methyl)-1-methyl(cyclopropyl)-4-nitro-5Н-pyrido[4,3-b]indoles containing substituents in the pyridine ring. A new scheme was developed for the synthesis of the starting 1-[6-aryl(methyl)-2-methyl(cyclopropyl)- 3-nitropyridin-4-yl]-1Н-1,2,3-benzotriazoles: 1) ammonolysis of 3-nitroisonicotinic acid ethyl esters, 2) a modified Hofmann reaction of 3-nitroisonicotinamides, 3) cleavage of ethyl (2-aryl-3-nitropyridin-4-yl)carbamates, 4) synthesis of 4-chloro-3-nitropyridines by diazotation reaction of 4-amino-3-nitropyridines, followed by nucleophilic substitution of diazo group in 4-pyridyldiazonium salts with a chlorine atom.

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This work received financial support from the Russian Foundation for Basic Research (grant 16-43-550144r_a) and from the Ministry of Education of the Omsk region.

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Authors and Affiliations

  1. F. M. Dostoyevsky Omsk State University, 55а Mira Ave., Omsk, 644077, Russia

    Vladislav Yu. Shuvalov, Alexander N. Shestakov, Lyudmila A. Kulakova, Anna K. Kuratova, Marina A. Vorontsova & Galina P. Sagitullina

  2. Omsk State Technical University, 11 Mira Ave., Omsk, 644050, Russia

    Vladislav Yu. Shuvalov

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  1. Vladislav Yu. Shuvalov
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  2. Alexander N. Shestakov
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  3. Lyudmila A. Kulakova
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  4. Anna K. Kuratova
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  5. Marina A. Vorontsova
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  6. Galina P. Sagitullina
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Correspondence to Galina P. Sagitullina.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(9), 844–850

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Shuvalov, V.Y., Shestakov, A.N., Kulakova, L.A. et al. Synthesis of 4-nitro-γ-carbolines by Graebe–Ullmann reaction. Chem Heterocycl Comp 55, 844–850 (2019). https://doi.org/10.1007/s10593-019-02547-w

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  • DOI: https://doi.org/10.1007/s10593-019-02547-w

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