AZINYL SULFIDES .27. REACTIONS OF 4-METHOXY-3-QUINOLINYL AND 1,4-DIHYDRO-4-OXO-3-QUINOLINYL SULFIDES AIMING AT THE SYNTHESIS OF 4-CHLORO-3-QUINOLINYL SULFIDES

The preparation of 1,4-dihydro-4-oxo-3'-alkylthio-3,4'-diquinolinyl su lfides 3 or 1,4-dihydro-4-oxo-3-(alkylthio)quinolines 4 by acid cataly sed hydrolysis of 4-methoxy-3'-alkylthio-3,4'-diquinolinyl sulfides 1 or 4-methoxy-3-(alkylthio)-quinolines 2 is described. The reactions of 4-methoxy-3'-alkylthio-3,4'-diquinolinyl sulfides 1 or 1,4-dihydro-4- oxo-3'-alkylthio-3,4'-diquinolinyl sulfides 3 with phosphoryl chloride in DMF afforded 4-chloro-3'-alkylthio-3,4'-diquinolinyl sulfides 5. T reatment of the title compounds 1 or 3 with boiling phosphoryl chlorid e systems:leads to 4-chloro-3-(alkylthio)quinolines 6 and thioquinanth rene but those of alkoxy- or oxo-quinolines 2 or 4 lead to 4-chloro-3- (alkylthio)quinolines 6. The reactions of N-methyl-4(1H)-quinolinones 3n and 4n with phosphoryl chloride directed to 4-chloro-3-(alkylthio)q uinolines 6 were studied as well.