Crotonic,cynnamic, and propiolic acids motifs in the synthesis of thiopyrano[2,3-d][1,3]thiazoles via hetero-Diels–Alder reaction and related tandem processes

Various novel thiopyrano[2,3-d][1,3]thiazol-2-one-6-carboxylic acids derivatives were synthesized in 54–86% yields via hetero-Diels–Alder reactions and related acylation-based tandem processes of 5-arylidene-4-thioxo-2-thiazolidinones with crotonic, propiolic, and cynnamic acids derivatives. Stereo- and regioselectivity of cycloaddition were investigated.     

Synthesis and Anticancer Activity of 2-Cyano-N-(furan-2-ylmethyl)-2-(4-oxo-3-arylthiazolidin-2-ylidene)acetamide Derivatives

Russian Journal of Organic Chemistry - 2-(4-Oxo-3-arylthiazolidin-2-ylidene)acetamide derivatives were prepared by the reaction of 2-cyano-N-furan-2-ylmethyl-3-sulfanyl-3-arylaminoacrylamides with...     

Synthesis and Primary Antitumor Screening of 4-[5-(1H-Indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamides

Russian Journal of Organic Chemistry - A preparative procedure was developed for the synthesis of 4-[5-(1-R-1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acids which...     

Synthesis of isothiocoumarin derivatives

A method was developed for the synthesis of 1-oxo-1H-isothiochromenes from 2-benzofuran-1(3H)-one (phthalide). 3-Bromo-6-chloro- and 3,6-dibromo-2-benzofuran-1(3H)-ones were prepared by the bromination of 6-chloro- and 6-bromo-2-benzofuran-1(3H)-ones and were converted by hydrolysis into 5-chloro- or 5-bromo-2-formylbenzoic acids. The condensation of these acids with rhodanine followed by recyclization gave 7-chloro- and 7-bromo-1-oxo-1H-isothiochromene-3-carboxylic acids.     

Synthesis and reactions of 5-aryl-2-thiophenecarbaldehydes

The reaction of 2-thiophenecarbaldehyde with arene diazonium chlorides in the presence of CuCl₂ catalyst gave 5-aryl-2-thiophenecarbaldehydes. Use of 4-nitrobenzene diazonium chloride in the reaction also gave the isomeric 3-(4-nitrophenyl)-2-thiophenecarbaldehyde. Condensation products of the 5-aryl-2-thiophenecarbaldehydes with cyanoacetic acid esters, cyanoacetamide, and with barbituric and dimethylbarbituric acids were prepared. Communication 16 in the series “Synthesis of heterocycles based on the products of arylation of unsaturated compounds”. For Communication 15 see [1]. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1166–1171, August, 2008.     

Reaction of Carboxylic Acid Hydrazides with 2,2′-(Carbonothioyldisulfanediyl)diacetic acid in Water as a “Green” Synthesis of N-(4-Oxo-2-sulfanylidene-1,3-thiazolidin-3-yl) Carboxamides

Russian Journal of Organic Chemistry - N-(4-Oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)benzamides were synthesized by reaction of substituted benzohydrazides with...     

Synthesis of 1H-1,2,3-triazole derivatives by the cyclization of aryl azides with 2-benzothiazolylacetonone, 1,3-benzo-thiazol-2-ylacetonitrile,and (4-aryl-1,3-thiazol-2-yl)acetonitriles

The cyclization of aryl azides with 2-benzothiazolylacetone, 1,3-benzothiazol-2-ylacetonitrile, and (4-aryl-1,3-thiazol-2-yl)acetonitriles in methanol in the presence of sodium methylate gives high yields of new products, 2-(5-methyl(amino)-1-aryl-1H-1,2,3-triazol-4-yl)-1,3-benzothiazoles and 1-aryl-(4-aryl-1,3-thiazol-2-yl)-1H-1,2,3-triazole-5-amines. 1,3-Benzothiazol-2-ylacetonitrile undergoes an anionic domino reaction with methyl 2-azidobenzoate or 2-azidobenzonitrile to give [1,2,3]triazolo[1,5-a]quinazoline derivatives. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 612–618, April, 2009.