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Unexpected sulfuration reaction of 1-substituted azulenes

✍ Scribed by Joye A. Billow; Tully J. Speaker

Publisher
John Wiley and Sons
Year
1975
Tongue
English
Weight
311 KB
Volume
64
Category
Article
ISSN
0022-3549

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✦ Synopsis

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.

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## Abstract 1‐(Bromoacetyl)‐3‐methylazulene **(1a)** and methyl 3‐(bromoacetyl)azulene‐1‐carboxylate **(1b)** reacted with thioamides **3a,b** and thioureas **3c,d** in boiling ethanol to give the corresponding (4‐thiazolyl)azulenes **4a‐d** and **5a‐d** in good yields, respectively. The reactions