Reactions of N-phenyl-3-oxobutanethioamide with 3-aryl-2-propenoyl chlorides in acetone in the presence of potassium carbonate give rise to 4-aryl-5-acetyl-1-phenyl-6-thioxopiperidin-2-ones, 2-aryl-5-acetyl-6phenylamino-2,3-dihydro-4H-thiopyran-4-ones, and 6-aryl-2-acetonylidene-3-phenyl-5,6-dihydro-4H-1,3-thiazin-4-ones whose structure was proved both by spectral methods and chemical transformations.
Chlorides. -The cycloacylation of thioamide (I) with 3-aryl-2-propenoyl chlorides (II) affords thiooxopiperidinones (III) along with minor amounts of either thiopyranones (IV) or thiazinone (V). -(BRITSUN, V. N.; BORISEVICH, A. N.; SAMOILENKO, L. S.; LOZINSKII, M. O.; Russ.
The nitrosation of N-aryl-3-oxobutanethioamides afforded 1-(6-R-benzothiasol-2-yl)-1-hydroxyimino-2-propanones that at oximation with hydroxylamine were converted into 1-(6-R-benzothiazol-2-yl)-1,2-dihydroxyiminopropanes. The latter were dehydrated by heating with succinic anhydride at 140°C yielding therewith 3-(6-Rbenzothiazol-2-yl)-4-methyl-1,2,5-oxadiazoles.
Reaction of α-Phenylaminomethylene-β-ketothionobutyric Acid Arylamides with α-Halo Carbonyl Compounds.-The title reaction produces the thiophenes (III), (V), or (VII) and ( VIII) depending on the substituents. -(BORISEVICH, A. N.; LOZINSKII, M. O.; SAMOILENKO, L. S.; RODIONOV, A. P.; Ukr. Khim. Zh. (Russ. Ed.) 56 (1990) 9, 971-975; Inst. org. khim. AN Ukr. SSR, Kiev, USSR; RU)
Synthesis of Substituted 2-Amino-4-methylpyrimidines from Arylamides of α-Phenylaminomethylene-β-ketothiobutanoic Acid.-The phenylaminomethylenebutanethioamide (I) reacts with guanidinium carbonate to give the 2-aminopyridinecarbothioamide (III). This product is converted to the hydrazide imide (IV), the thiosemicarbazide (VI), the pyrazolopyrimidine (VIII), and the hydrazone (IX). -(SAMOILENKO, L. S.; FILONENKO, L. P.; BORISEVICH, A. N.; LOZINSKII, M. O.; Ukr. Khim. Zh. (Russ. Ed.) 57 (1991) 4, 409-414; Inst. org. khim. AN Ukr. SSR, Kiev; RU)
Oxadiazole derivatives R 0290Synthesis of 3-(6-R-Benzothiazol-2-yl)-4-methyl-1,2,5-oxadiazoles. -A high-yielding three-step procedure for the synthesis of oxadiazoles (IV) is developed. The benzothiazole ring formation proceeds simultaneously during nitrosation of the activated methylene group in the starting compound (I). -(BRITSUN, V. N.; BORISEVICH, A. N.; SAMOILENKO, L. S.; LOZINSKII, M. O.; Russ. J. Org. Chem. 41 (2005) 5, 745-747; Inst. Org. Chem., Acad. Sci. Ukr., Kiev 253094, Ukraine; Eng.) -R. Staver 51-115
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