A method has been developed for the synthesis of 2,3'-biquinolines based on the reaction of β-(2-quinolyl)-2-aminostyrenes with acid amides under Vilsmeier reaction conditions.A series of methods for the synthesis of 2,3'-biquinolines 2 has been developed which includes either formation of quinoline rings (e.g. in [2-5]) or of a bond between them [6, 7]. These methods have a number of drawbacks which include the low availability of starting compounds or the possibility of synthesizing only symmetrically substituted 2,3'-biquinoline derivatives.In this work we report a method for the synthesis of 2,3'-biquinolines which allows one to synthesize, from one starting compound, 2,3'-biquinolines with different substituents in the 2'-position.We have shown that the reaction of the amines 1a,b with DMF or the diethylamides of other carboxylic acids in the presence of POCl 3 gives high yields (82-88%) of the 2,3'-biquinolines 2a-f. N N R X N N H 2 X 1a,b 2a-f 1) RCONR 1 2 /POCl 3 2) H 2 O 1 a X = H, b X = NO 2 ; 2 a R = H, b R = Me, c R = Pr, d R = Bu, e R = Ph; a-e X = H, f R = H, X = NO 2The reaction of the amine 1 with acid chlorides in the presence of Et 3 N and subsequent treatment with POCl 3 occurs similarly. In this case the yields of the reaction products are lower.
Synthesis of 2,3'-Biquinolines by Cyclization of β-(2-Quinolyl)-2-aminostyrenes. -(LYAKHOVNENKO, A. S.; TRIFONOV, V. V.; GONCHAROV, V. I.; AKSENOV, A. V.; Chem. Heterocycl. Compd. (N. Y.) 42 (2006) 9, 1205-1207; Stavropol State Univ., Stavropol' 355009, Russia; Eng.) -R. Langenstrassen 21-127
Quinoline derivatives R 0410Novel Approach to Synthesis of 1',4'-Dihydro-2,3'-biquinolines -[from accessible quinoline derivatives]. -(TRIFONOV, V. V.; AKSENOVA, I. V.; GONCHAROV, V. I.; AKSENOV, A. V.; Chem. Heterocycl. Compd. (N. Y.) 41 (2005) 12, 1541-1542; Stavropol State Univ., Stavropol' 355009, Russia; Eng.) -H. Toeppel 32-175
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