Preparative synthesis of 4-methyl-2-(trifluoromethyl)-1,3-oxazin-6-one

Russian Chemical Bulletin -     

Photochemistry of 4-phenyl-1,3-dioxolan-2-one

The photolysis of the mono substituted cyclic carbonate ester 4-phenyl-1,3-dioxolan-2-one has been studied. The direct irradiation results in loss of carbon dioxide with the formation of the corresponding ox-irane, styrene oxide as well as phenylacetaldehyde and bibenzyl. Photolysis in methanol produces the same compounds in addition to phenethyl alcohol and 2-methoxy-2-phenylethanol. Triplet sensitized photolyses resulted in the products derived entirely from benzyl radicals with none of the oxirane being detected.     

Synthesis of 3-[4-(1-Benzofuran-2-yl)-1,3-thiazol-2-yl]-2-(4-aryl)-1,3-thiazolidin-4-one Derivatives as Biological Agents

A protocol for the synthesis of 3-[4-(1-benzofuran-2-yl)-1,3-thiazol-2-yl]-2-(4-aryl)-1,3-thiazolidin-4-one derivatives (5a–e) has been developed from 1-(1-benzofuran-2-yl)-2-bromoethanone (2),which served as a key intermediate for the synthesis of the title compounds. The reaction of compound 2 with thiourea furnished 4-(1-benzofuran-2-yl)-1,3-thiazol-2-amine 3, which upon further reaction with various aromatic aldehydes, gave Schiff bases 4a–e. These Schiff bases, when treated with thioacetic acid in the presence of catalytic amount of anhydrous ZnCl₂, yielded thiazolidinone derivatives 5a–e. All the newly synthesized compounds have been characterized by analytical and spectral data and screened for their antimicrobial and analgesic activity.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

Synthesis of 2-sulfanylidene-1,3-thiazolidin-4-one derivatives

Three-component condensation of primary amines with carbon disulfide and dialkyl maleates afforded the corresponding alkyl (3-R-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-yl)acetates whose structure was confirmed by independent synthesis and IR and ¹H NMR spectroscopy.     

Synthesis of 2-thioxo-1,3-thiazolidin-4-one derivatives

A series of new 2-thioxo-1,3-thiazolidin-4-one derivatives containing arylidene, arylazo, and aminomethylene fragments in position 5 of the rhodanine cycle was synthesized. Dedicated to Academician V. A. Tartakovsky on the occasion of his 75th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1564–1569, August, 2007.     

1,3-Dipolar cycloaddition of diarylnitrones to 1-(4-nitrophenyl)-5H-pyrrolin-2-one

The reaction of diarylnitrones with 1-(4-nitrophenyl)-5H-pyrrolin-2-one to give 2-oxa-6-oxo-3-phenyl-4-(R-phenyl)-7-(4-nitrophenyl)-3,7-diazabicyclo(3,3,0)octanes has been examined. The structures of the products were established by NMR and IR spectroscopy, and x-ray diffraction studies. The stereoselectivity of the reaction is due to exo-approach of the reactants with cis-stereospecific addition of the trans-forms of the C,N-diarylnitrones to the pyrrolinone double bond.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1675–1678, December, 1990.     

A convenient method for the synthesis of 2-[(5-benzyl-1,3-thiazol-2-yl)imino]-1,3-thiazolidin-4-one derivatives

It was found that the reaction of 2-chloroacetamido/chloropropioamido-5-benzylthiazole with potassium thiocyanate gave, via rearrangement, 2-[(5-benzyl-1,3-thiazol-2-yl)imino]-1,3-thiazolidin-4-ones.     

Synthesis of 1-trichloeoacetyl-2-teichloeomethyl-1,3-diaza-2-cyclobuten-4-one

Conclusions Trichloroacetyl isocyanate reacts with trichloroacetonitrile on the type of 22-cycloaddition with the formation of 1-trichloroacetyl-2-trichloromethyl-1,3-diaza-2-cyclobuten-4-one.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimichesckaya, No. 10, pp. 2325–2326, October, 1972.     

Addition reactions of 2-polyfluoroalkyl substituted 1,3-thiazolin-4-one derivatives

2-Polyfluoroalkyl-5-methoxycarbonylmethylene-thiazolin-4-ones react as dienophiles on the exo-cyclic ylidene bond to give spiro-derivatives and as 1,3-dienes with olefins to give dihydropyranothiazole derivatives. The endo-cyclic CN bond in these compounds do not enter into the cycloaddition reactions.