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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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. Stravropol State University, Stavropol, 355009, Russia

    A. V. Aksenov, N. V. Demidova & O. P. Demidov

  2. Stavropol State Medical Academy, Stavropol, 355017, Russia

    V. I. Goncharov

Authors
  1. A. V. Aksenov
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  2. N. V. Demidova
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  3. O. P. Demidov
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  4. V. I. Goncharov
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Correspondence to A. V. Aksenov.

Additional information

*For Communication 25 see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 578-585, April, 2009.

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Aksenov, A.V., Demidova, N.V., Demidov, O.P. et al. 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. Chem Heterocycl Comp 45, 454–460 (2009). https://doi.org/10.1007/s10593-009-0285-8

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  • DOI: https://doi.org/10.1007/s10593-009-0285-8

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