Chemistry of heterocyclic compounds at the Institute of Organic Chemistry,National Academy of Sciences of Ukraine (Review)

The present work is dedicated to the 70th anniversary of the Institute of Organic Chemistry, National Academy of Sciences of Ukraine. It contains a review of achievements in the chemistry of heterocyclic compounds, a brief historical account, and information on the work of the Institute’s team in recent years. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 485–513, April, 2009.     

2-R-5-Ar(Het)-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones

A novel method for synthesis of 2-R-5-Ar(Het)-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones by condensation of 3-R-4,5-dihydro-1H-1,2,4-triazole-5-thiones with 3-aryl(heteryl)-2-propenoyl chlorides is proposed.     

Synthesis and Properties of 1,3-Diaryl-5,6-dihydro-8H-imidazo[2,1-c]-1,4-oxazinium Bromides

It has been established that the condensation of 3-(4-methoxyphenylamino)-5,6-dihydro-2H-1,4-oxazine with substituted phenacyl bromides occurs at the exocyclic nitrogen atom with formation of 3-aryl-3-hydroxy-1-(4-methoxyphenyl)-2,5,6,8-tetrahydro-3H-imidazo[2,1-c]-1,4-oxazinium bromides. By treatment of the latter with acetic anhydride 3-aryl-1-(4-methoxyphenyl)-5,6-dihydro-8H-imidazo[2,1-c]-1,4-oxazinium bromides are formed. The structures of the compounds synthesized were determined via ¹H NMR spectroscopy and X-ray diffraction.     

Structure of the Reaction Product of Anthranilic Acid Hydrazide with Carbon Disulfide in Alkaline Medium

The reaction of anthranilic acid hydrazide with carbon disulfide in alkaline medium yields 5-(2-aminophenyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione rather than 3-amino-2-thioxo-1,2,3,4-tetrahydroquinazolin-4-one. The structure of the product was proved by spectral methods and chemical transformations.     

Synthesis of 4-Amino-6-R-4,5-dihydro-3-phenacylthio-1,2,4-triazin-5-ones and 8H-3-R-7-Aryl-1,2,4-triazino[3,4-b][1,3,4]thiadiazin-4-ones

A study was carried out on the reaction of 4-amino-6-R-2,3,4,5-tetrahydro-3-thioxo-1,2,4-triazin-5-ones with halo ketones in alkaline media to yield 4-amino-6-R-4,5-dihydro-3-phenacylthio-1,2,4-triazin-5-ones, which then convert to 8H-3-R-7-aryl-1,2,4-triazino[3,4-b][1,3,4]thiadiazin-4-ones.     

Synthesis and reactions of 1-R-3-benzoyl-5-ethoxycarbonyl-6-oxo-1,2,3,6-tetrahydropyridine-2-thiones

Cycloacylation of N-R-3-oxo-3-phenylpropanethioamides by diethyl ethoxymethylenemalonate occurs selectively to form 1-R-3-benzoyl-5-ethoxycarbonyl-6-oxo-1,2,3,6-tetrahydropyridine-2-thiones which are convenient starting materials for the synthesis of bi-and tricyclic hetero systems including the previously unknown 9-R-7-ethoxycarbonyl-5-phenyl-8,9-dihydropyrido[2,3-d][1,2,4]triazolo[1,5-a]-pyrimidin-8-ones. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1660–1669, November, 2007.