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2004
Fused pyridine derivatives
R 0450
Novel Tandem Hydration/Cyclodehydration of α-Thiocyanatoketones to 2-OxoApplication to Thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione
51- 118 -3-thiazolines.
Synthesis. — Thiocyanates are converted to the title thiazoloquinolines by treatment
with conc. H2SO 4/AcOH. The primarily formed thiocarbamates [cf. (VI)] are cyclodehydrated in situ. Concentrated sulfuric acid is found to be critical for the reaction as
both thiocyanates and thiocarbamates are rapidly hydrolyzed in the presence of water
to give hydroxyquinolinones. — (KLASEK*, A.; MRKVICKA, V.; PEVEC, A.;
KOSMRLJ, J.; J. Org. Chem. 69 (2004) 17, 5646-5651; Dep. Food Eng. Chem., Fac.
Technol., Tomas Bata Univ., CZ-762 72 Zlin, Czech Republic; Eng.) — Klein
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