Unexpected sulfuration reaction of 1-substituted azulenes.
Azulenes reacted unexpectedly and readily with thionyl chloride to give sulfonic acid chlorides and bisthioethers. The sulfonic acids but not the thioethers have antibacterial activity.
D052176:Azulenes; D001419:Bacteria / Q000187:drug effects; D003508:Cycloheptanes / Q000494:pharmacology; D003517:Cyclopentanes / Q000494:pharmacology; D013449:Sulfonamides / Q000138:chemical synthesis / Q000494:pharmacology; D013451:Sulfonic Acids / Q000138:chemical synthesis / Q000494:pharmacology; D013871:Thiones / Q000138:chemical synthesis / Q000494:pharmacology
D052176:Azulenes; D003508:Cycloheptanes; D003517:Cyclopentanes; D013449:Sulfonamides; D013451:Sulfonic Acids; D013871:Thiones; C005525:azulene