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2005
Thiazole derivatives
R 0260
A New Synthesis of Thiazole Derivatives via Ring Transformation of 6-ImiHydroperchlorates. — The use of the title hydroperchlorates
08- 130 no-6H-1,3-thiazine
(I), (V), and (VII) offers the opportunity to prepare 2-arylthiazoles with a cyanoacetate
group at position 4. Hydroperchlorates (I) are converted into thiazoles (III) by reaction
with acceptor-substituted halomethanes (II). The thiazole preparation is a synthesis of
the C + S—C—N—C type and yields compounds having an acceptor group at position
5. Thus, this method provides thiazoles with a carbonyl, ester or cyano group in position
5 and a cyanoacetate group at position 4. The aryl substituent is responsible for a distinguished reaction course in some cases, cf. (VI) and (VIII). Thiazolopyridine (IV) is
tested for its inhibiting properties on the TNF-α-production after stimulation with
lipopolysaccharides in monocytes. Depending on the concentration, an inhibition
behavior is measurable. — (BRIEL, D.; Heterocycles 63 (2004) 10, 2319-2328; Inst.
Pharm. Pharm. Chem., Univ. Leipzig, D-04103 Leipzig, Germany; Eng.) —
H. Hoennerscheid
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