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

Abstract

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.

How to Cite
Aksenov, A. V.; Demidova, N. V.; Demidov, O. P.; Goncharov, V. I.  Chem. Heterocycl. Compd. 2009, 45, 454. [Khim. Geterotsikl. Soedin. 2009, 578.]

For this article in the English edition see DOI 10.1007/s10593-009-0285-8