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Chemistry of Heterocyclic Compounds

, Volume 45, Issue 4, pp 454–460 | Cite as

The investigation in 2,3'-biquinoline series 26.* Regioselective nitration of 1'-alkyl-1',4'-dihydro-2,3'-biquinolin-4'-ones and 1'-alkyl-1',2'-dihydro-2,3'-biquinolin-2'-ones

  • A. V. Aksenov
  • N. V. Demidova
  • O. P. Demidov
  • V. I. Goncharov
Article

The nitration of 1'-alkyl-1',4'-dihydro-2,3'-biquinolin-4'-ones and 1'-alkyl-1',2'-dihydro-2,3'-biquinolin-2'-ones has been investigated. It was shown that the regioselectivity of nitration of the first depends on the acidity of the medium and the order of adding reactants. In strongly acidic medium 1'-alkyl-5,6'-dinitro-1',4'-dihydro-2,3'-biquinolin-4'-ones or mixtures of them with 1'-alkyl-5-nitro-1',4'-dihydro-2,3'-biquinolin-4'-ones are formed. In less acidic media 1'-alkyl-6'-nitro-1',4'-dihydro-2,3'-biquinolin-4'-ones and then 1'-alkyl-6,6'-dinitro-1',4'-dihydro-2,3'-biquinolin-4'-ones are formed. Nitration of 1'-alkyl-1',2'-dihydro-2,3'-biquinolin-2'-ones leads to 1'-alkyl-6'-nitro-1',2'-dihydro-2,3'-biquinolin-2'-one and then 1'-alkyl-6,6',8'-trinitro-1',2'-dihydro-2,3'-biquinolin-2'-one.

Keywords

1'-alkyl-1',2'-dihydro-2,3'-biquinolin-2'-ones 1'-alkyl-1',4'-dihydro-2,3'-biquinolin-4'-ones 2,3'-biquinoline nitro-1'-alkyl-1',4'-dihydro-2,3'-biquinolin-4'-ones nitro-1'-alkyl-1',2'-dihydro-2,3-bi-quinolin-2'-ones nitration regioselectivity 

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Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • A. V. Aksenov
    • 1
  • N. V. Demidova
    • 1
  • O. P. Demidov
    • 1
  • V. I. Goncharov
    • 2
  1. 1.Stravropol State UniversityStavropolRussia
  2. 2.Stavropol State Medical AcademyStavropolRussia

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