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

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2009-04, Vol.45 (4), p.454-460
• Main Authors: Aksenov, A. V, Demidova, N. V, Demidov, O. P, Goncharov, V. I
• Format: Article
• Language: English
• Subjects: 1'-alkyl-1',2'-dihydro-2,3'-biquinolin-2'-ones; 1'-alkyl-1',4'-dihydro-2,3'-biquinolin-4'-ones; 2,3'-biquinoline; Chemistry; Chemistry and Materials Science; nitration; nitro-1'-alkyl-1',2'-dihydro-2,3-bi-quinolin-2'-ones; nitro-1'-alkyl-1',4'-dihydro-2,3'-biquinolin-4'-ones; Organic Chemistry; Pharmacy; regioselectivity
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-009-0285-8

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.