140868-77-5Relevant academic research and scientific papers
1,2-Thiazoles by Ring Transformation of 2H-Thiopyran-2-thiones
Schweiger, Klaus,Schubert-Zsilavecz, Manfred,Weis, Robert,Belaj, Ferdinand
, p. 133 - 144 (1992)
Aminolyses of 4-dialkylamino-2-methylthiothiopyranes halides with ammonia leads to 4-amino-2-dialkylaminothiopyranylium halides.On treatment with alkali these products are hydrolyzed to N,N-dialkyl-3-amino-2,4-hexadienthioamides, which react with peroxide under oxidative cyclization to 5-dialkylamino-1,2-thiazoles.In order to determine the structures of the unsaturated thioamides and isothiazoles 13C-NMR-spectroscopic analysis and a single crystal X-ray structure analysis of 5-dimethylamino-3-(2-methyl-1-propenyl)-1,2-thiazole (6a) at 100 K were carried out.C9H14N2S, Mr = 182.28, monoclinic, P 21/a, a = 11.622(2), b = 6.303(1), c = 13.678(2), β = 104.49(3) deg, V = 970.1(3) Angstroem3, Z = 4, dx = 1.248 g/cm3, μ = 27.0 mm-1, R = 4.93percent, Rw = 4.84percent (1672 observations, 157 parameters).Keywords: Oxidative cyclization; 1,2-Thiazoles; 13C-NMR-data; X-Ray analysis.
