New syntheses of 5,6- and 7,8-diaminoquinolines

Abstract

The synthesis of 5,6- and 7,8-diaminoquinoline derivatives starting from angularly annelated selenadiazoloquinolones is presented. Simple chlorination of the pyridone ring followed by reductive deselenation of the 1,2,5-selenadiazole ring afforded novel 4-chloro-o-diaminoquinolines. Dechlorination of 4-chloro-7,8-diaminoquinoline gave 7,8-diaminoquinoline hydrochloride which was successfully employed as starting material in the synthesis of condensed nitrogen heterocycles.

Keywords

• chlorination
• deselenation
• nitrogen heterocycles
• o-diaminoquinolines
• selenadiazoloquinolones