NUCLEOPHILIC-SUBSTITUTION OF 2,4-DICHLOROQUINOLINE-3-CARBONITILE WITHDIFFERENT NUCLEOPHILES - SYNTHESIS OF SEVERAL NEW QUINOLINE-3-CARBONITRILE DERIVATIVES

2,4-Dichloroquinoline-3-carbonitrile (1) reacted with several nucleoph iles produced a novel substituted quinolines. Nucleophilic substitutio n of 1 with thiolate anions leads to the thio ethers 2a-c. Acid hydrol ysis of 2a afforded the corresponding 4-quinolinones 3. The amino-quin oline 5a,b; 7a,b and pyrazoloquinoline 9 are prepared by nucleophilic substitution of 1 with amines and N2H4, respectively. Nucleophilic sub stitution of 1 with azide anion yielded the azidoquinoline 10, which r eacted with H-2/Pd and PPh3 to give the quinoline derivatives 13a-c.