Azinyl sulfides .38. 4-quinolinyl selenides with 3-substituents of alkylthio-type or with 3-chloro ones

Syntheses of 4-(methylseleno)-3-(methylthio)- or 3-chloroquinolines 1a,b and 3,3'-disubstituted (methylthio- or chloro)-4,4'-diquinolinyl selenides 2a,b from 4-chloro-3-substituted quinolines 6a,b and selenourea were described. 1,3-Thiaselenolo[5,4-c]quinolines 3a and 3b were synthesized from 4-chloro-3-(chloromethylthio)quinoline 7 and from 4-chloro-3-(vinylthio)quinoline 8 and selenourea, respectively. Attempts of the synthesis of 2,3-dihydro-1,4-thiaselenino[6,5-c]quinoline 5 from sodium 3-(vinylthio)-4-quinolineselenide have failed. (II)-I-1 NMR data of 4-quinolinyl selenides show that selenide induced peri-substituent effect is lower than that of sulfide one.