V. A. Sedavkina

3-Arylidene derivatives of 3H-furan-2-ones. Synthesis and reaction with maleic anhydride

The synthesis of 5-alkyl(aryl)-3-arylidene-3H-furan-2-ones was accomplished, and their reaction with maleic anhydride was studied. The configuration of the initial arylidene derivatives was established on the basis of the PMR spectra of the adducts obtained.

Synthesis and antimicrobial properties of Mannich bases in the 2-pyrrolidone and 2-thiopyrrolidone series

It has been found that N-alkylpyrrolidones do not undergo the Mannich reaction. Reaction is observed only following the introduction of an acetyl group at the pyrrolidone ring nitrogen (lla-c). However, replacement of the carbonyl group by thiocarbonyl increases C--H acidity in the 2-thiopyrroiidones, with the result that the 2-thiopyrrolidone (Ib) reacts with formaldehyde and secondary amines (dimethylamine, morpholine, piperidine, and pyrrolidine) to give compounds (lid-g).

Synthesis of 5-alkyl-3H-thiolen-2-ones and 5-alkyl-3H-furan-2-ones and condensation reactions at the heterocyclic methylene group

The intramolecular cyclization of γ-ketocarboxylic acids and their esters gives 5-alkylsubstituted 3H-thiolen-2-ones and 3H-furan-2-ones. It was shown that reaction occurred at the heterocyclic methylene group and that the conditions under which the reaction took place depended on the nature of the heterocyclic atom.

Substitution of 3H-furan-2-ones in amination and hydroamination reactions

The amination and hydroatnination of 5-alkyl-3H-furan-2-ones and their 3-benzylidene- and 3 formyl-derivatives were studied. The characteristics of the reactions, the requirements for the nature of the nucleophilic reagents, and the reaction conditions leading to the destruction of the furan ring and recyclization to pyrrolidinone and pyrrolinone structures are indicated.

Bromination of 5-Substituted 3H-Furan-2-ones and 3H-Pyrrol-2-ones

The bromination of 5-alkyl(aryl)-3H-furan-2-ones and 5-alkyl(aryl)-3H-pyrrol-2-ones and also their derivatives takes place at the ethylene bond with the formation of 4-monobromo derivatives. N-Phenyl-3H-pyrrol-2-ones are brominated simultaneously at the ethylene bond of the heterocycle and at the phenyl substituent at the nitrogen atom.

Heterocyclization of derivatives of 4-oxoalkanoic acids to 1,5-disubstituted pyrrolin-2-ones

Conditions were developed for the synthesis and production of 1-aryl-5-alkyl(aryl)-3H- and 1-aryl-5-alkyl(aryl)-5H-pyrrolin-2-ones from the amides and esters of 4-oxoalkanoic acids. It was established that the yield and ratio of the 3H and 5H isomers depend on the substrate employed in the reaction.

Synthesis and antimicrobial activity of morpholine derivatives of 2-pyrrolidones and their thio analogs

!. B.A. Zhubanov, I. A. Arkhipova, and O. A. Almabekov, Thermally Stable Heterocyclic Polymers [in Russian], Alma-Ata (1979). 2. B.A. Zhubanov, I. A. Arkhipova, and M. B. Leonova, Izv. Akad. Nauk Kazakh SSR, Ser. Khim., No. 2, 55 (1987). 3. V.P. Chernykh, A. N. Brizitskaya, u I. Kabachnyi, et al., Conference of Pharmacists of the Ukrainian SSR, No. 4. Abstracts of Reports [in Russian], Zaporozhe (1984), p. 131. 4. H.M. Deutsch, L. T. Gelbaum, M. Laughlin~ et al., J. Med. Chem., 29, 2164 (1986). 5. R. Pettit, K. D. Paull, C. L. Herald, et al., Can. J. Chem., 61, No. I0, 2291 (1983).

Synthesis and antimicrobial activity of certain derivatives of N-substituted pyrrolidones and pyrrolidines

(1975). 8. T. Sieta, K. Yamauch, and M. Imoto, Bull. Chem. Soc. Jpn., 45, 926-928 (1972). 9. K.L. Carraway, P. C. Huang, and T. G. Scott, Synth. Proc. Nucleic Acid. Chem., i, 3-5 ( 1 9 6 8 ) . i0. E. L. M. Pattison, W. C. Howell, A. J. McNamara, et al., J. Org. Chem., 21, 739-747 (1956). ii. J.W. Farren, H. R. Fife, F. E. Clark, et al., J. Am. Chem. Soc., 47, 2419-2423 (1925). 12. R. A. Meikeljohn, R. J. Meyer, S. M. Aronovic, et al., Anal. Chem., 29, 329-324 (1957). 13. L. Bellamy, Infrared Spectra of Complex Molecules [Russian translation], Moscow (1963). 14. G. H. Beaven, E. R. Holiday, and E. A. Johnson, Spectrochim. Acta, i, 338-347 (1951). 15. J. K. Coward and W. D. Suced, J. Med. Chem., 15, 381-384 (1972).

Synthesis and Structure of 5-Alkyl(aryl)pyrrol-2-ones

The amination of 4-oxoalkanoic acids and their esters by the action of ammonia and ammonium acetate leads to the formation of N-unsubstituted 5-alkyl(aryl)pyrrol-2-ones, which exist in solution in the form of a mixture of isomers in a ratio depending on the nature of the substituent at position 5 of the heterocycle.

Antimicrobial activity of 5-alkyl-3H-furanones and their sulfur analogs

A study of the condensation of furanones I and thiophenones II with aldehydes showed regularities as a function of structure; the rate of reaction and the yields of arylidene derivatives showed the influence of the structures of the starting aldehydes. Thus, reaction with benzaldehyde and its chloroand nitro-substituents was less complicated in giving side reactions than reaction with furfurol.