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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 9, pp 844–850 | Cite as

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

  • Vladislav Yu. Shuvalov
  • Alexander N. Shestakov
  • Lyudmila A. Kulakova
  • Anna K. Kuratova
  • Marina A. Vorontsova
  • Galina P. SagitullinaEmail author
Article
  • 28 Downloads

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.

Keywords

4-amino-3-nitropyridines 1-[6-aryl(methyl)-2-methyl(cyclopropyl)-3-nitropyridin-4-yl]-1Н-1,2,3-benzotriazoles 3-aryl(methyl)- 1-methyl(cyclopropyl)-4-nitro-5Н-pyrido[4,3-b]indoles 4-chloro-3-nitropyridines ethyl (4-pyridyl)carbamates ethyl esters and amides of 3-nitroisonicotinic acid Graebe–Ullmann reaction 

Notes

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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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Vladislav Yu. Shuvalov
    • 1
    • 2
  • Alexander N. Shestakov
    • 1
  • Lyudmila A. Kulakova
    • 1
  • Anna K. Kuratova
    • 1
  • Marina A. Vorontsova
    • 1
  • Galina P. Sagitullina
    • 1
    Email author
  1. 1.F. M. Dostoyevsky Omsk State UniversityOmskRussia
  2. 2.Omsk State Technical UniversityOmskRussia

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