ISSN:
1434-4475
Keywords:
Oxidative cyclization
;
1,2-Thiazoles
;
13C-NMR-data
;
X-Ray analysis
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary 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 isothiazoles13C-NMR-spectroscopic analysis and a single crystal X-ray structure analysis of 5-dimethylamino-3-(2-methyl-1-propenyl)-1,2-thiazole (6 a) at 100K were carried out: C9H14N2S,M r=182.28, monoclinic, P 21/a,a=11.622(2),b=6.303 (1),c=13.678(2), β=104.49(3)°,V=970.1(3)Å3,Z=4,d x=1.248 g/cm3, μ=27.0 mm−1,R=4.93%,R w=4.84% (1 672 observations, 157 parameters).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01045306
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