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Synthesis of 1-(4-thiazolyl)azulenes: Reactions of bromoacetyl-substituted azulenes with thioamides, thioureas, and thiosemicarbazones

✍ Scribed by Hiromi Takao; Dao-Lin Wang; Shigeru Kikuchi; Kimiaki Imafuku

Publisher: Journal of Heterocyclic Chemistry
Year: 2004
Tongue: English
Weight: 227 KB
Volume: 41
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570410512

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✦ Synopsis

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 of dibromoacetyl‐substituted azulene (2) also gave (4‐thiazolyl) azulenes 5a‐d in lower yields and the azulene 2 was recovered. By heating compounds 5a‐d in 100% phosphoric acid, the ester group was eliminated to yield 1‐(4‐thiazolyl)azulenes 6a‐d. Compounds 1a,b reacted with thiosemicarbazones 7a‐f to afford [(2‐alkylidenehydrazino)thiazol‐4‐yl]azulenes 8a‐f and 9a‐f in moderate to high yields via their hydromides.

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