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2005
Thiazole derivatives
R 0260
Synthesis of 1-(4-Thiazolyl)azulenes: Reactions of Bromoacetyl-Substituted Azuwith Thioamides, Thioureas, and Thiosemicarbazones. — The reaction of
06- 127 lenes
azulenes (I) with thioamides and thioureas (II) are initiated by nucleophilic attack of
the sulfur atom on the methylene carbon of the bromoacetyl group to generate a thiazolyl ring. Reactions of the α,α-dibromonated ketone (IV) with (II) are retarded affording the same compounds albeit in lower yields. Heating of (IIId)—(IIIf) in 100% phosphoric acid leads to elimination of the ester group. Thiazolylazulenes (VII) are obtained
via their hydrobromides by reaction of (I) with thiosemicarbazones (VI). —
(TAKAO, H.; WANG, D.-L.; KIKUCHI, S.; IMAFUKU*, K.; J. Heterocycl. Chem.
41 (2004) 5, 723-729; Dep. Chem., Fac. Sci., Kumamoto Univ., Kurokami,
Kumamoto 860, Japan; Eng.) — H. Hoennerscheid
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