QUINOLINES WITH HETEROATOM SUBSTITUENTS IN POSITION-2 AND POSITION-4 - NUCLEOPHILIC-SUBSTITUTION OF 2,4-DICHLORO-3-PHENYLQUINOLINES

Thio ethers 2a-d and 4a-d are prepared by nucleophilic substitution of 2,4-dichloro-3-phenylquinoline 1 with thiolate anions. Acid hydroslys is of 2a-d afforded the corresponding 2-quinolinones 3a-d, while, on a cid hydrolysis of 4a-d, only 4a is converted to 4-mercapto-2-quinoline thione 5. Indolo-quinoline 7 was obtained by thermolysis of the corres ponding azido-quinoline 6, which was prepared by nucleophilic substitu tion of 2a with azide anion. Nucleophilic substitution of chloroquinol ine 1 with the sodium salt of 1,2,4-triazole yielded compound 8.