Synthetic Studies Using α,β-Unsaturated Nitriles: Facile Synthesis of Pyridine Derivatives

3-Aryl-2-sulfanylpropenoic acids as precursors for some novel (Z)-5-substituted-2-alkoxy-2-trichloromethyl-4-thiazolidinones

“…The structures of the products were confirmed by elemental analyses and spectral data (IR, 1 H NMR, 13 C NMR, MS and X-ray). For example, the IR spectrum of the isolated product 4a taken as a typical example of the series showed two absorption bands at ν 3388 and 3309 cm -1 corresponding to the amino group and one absorption band at 1751 cm -1 corresponding to lactone carbonyl group.…”

“…[1][2][3][4][5] Additionally, 3-aryl-2-sulfanylpropenoic acids have been found to be useful antidotes for heavy metal poisoning. For example, 3-furyl-2-sulfanylpropenoic acid in particular has been shown to protect against cadmium intoxication in rats.…”

Synthesis and reactions of (Z)-2-imino-5-(3,4,5-trimethoxy benzylidene)thiazolidin-4(H)one

“…Cyclohexyl magnesium bromide attacks 2-piperidino derivative 6 in refluxing ether-anhydrous benzene mixture through 1,2-addition at C=N to give (Z)-2-cyclohexyl-2-(piperidin-1-yl)-5-(3,4,5-trimethoxybenzylidene)-thiazolidin-4-one (8). The structure of 8 is substantiated by microanalysis which infers the addition of one molecule of cyclohexane and confirmed by IR spectrum which exhibits the strong absorption bands characteristic for NH (br.…”

“…The reaction of activated nitriles with 2-thiazolidine derivatives has previously claimed to afford the thiazolopyrimidine derivatives in moderate yield [8,9]. We report here that no thiazolopyrimidine 3' could be isolated in the reaction of α-cyano-3,4,5-trimethoxy cinnamonitrile and/or ethyl-α-cyano-3,4,5-trimethoxy cinnamate (1a,b) with 2-imino-4-oxo-2-thiazolidine 2 and instead we have found that the reaction product in all cases was 5-arylmethylene-2-imino-4-oxo-2-thiazolidine 3.…”

Synthesis and transformations of some 1,2,4-trisubstituted pyrroles

“…The second methoxycarbonyl group at N is twisted out of the pyrrole plane due to free rotation around the methylene group. 13 In connection with the new data about the synthesis of C-vinylpyrroles, 15 the series of substituted β-pyrolylalkenes 4-8 (Scheme 2) was obtained under the conditions of the Knoevenagel reaction of formyl ester 3b and various C-acids, such as ethyl hydrogen malonate, 16 diethyl malonate, (1,3-benzoxazol-2-yl)acetonitrile, 17 (1,3-benzothiazol-2-yl)acetonitrile, 18 (1H-benzimidazol-2-yl)acetonitrile, 19 N- (1,3-benzothiazol-2-yl)cyanoacetamide, 20a as well as its 6-methoxyderivative, 20b and malonodinitrile. Catalysed by piperidine, glycine, 10% ethanolic sodium ethoxide, and potassium acetate respectively, the reactions gave yields ranging from 50-97%.…”