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Diastereoselective Synthesis of 3,4-Dıbenzoil-3,4-Dihydro-1H-Spiro [Benzo[cd]Indol-5,3'-Indoline]-2,2’(2aH)-Diones

Year 2019, Volume: 1 Issue: 1, 20 - 23, 01.02.2019

Abstract

Diastereoselective syntheses of 3,4-dibenzoyl-3,4-dihydro-1H-spiro[benzo[cd]indole-5,3'-indoline]-2,2'(2aH)-dionesin boiling DMF have been carried out starting with 3-(2-phenyl-2-oxoethylidene)indolin-2-ones via a Diels-Alder addition reaction. Theoretical and practical investigations of structure-activity relationships in the group of synthesizedspirooxindoleshave been performed.

References

  • Macaev F., Geronikaki A., Sucman N. Recent application of isatins in synthesis of functionalized spirocyclicoxindoles. Chapter in „Targets in heterocycliic systems. Chemistry and Properties”. Ed. O. A. Attanasi and D. Spinelli. Italian Chemical Society, 2011, nr 15, 294-326.
  • Millemaggi A., Taylor R.J.K.3-Alkenyl-oxindoles: natural products, pharmaceuticals, and recent synthetic advances in tandem/telescoped approaches. Eur. J. Org. Chem. 2010, 24, 4527-4547.
  • HanschC.,Sammes P., Taylor J. Comprehensive Medicinal Chemistry. Oxford: Pergamon, 1990. vol. 6. 756 p.
  • Radul O., Junghietu G., Rehter M. Buhaniuk S.A simple way to obtain 1-substituted isatins. Chem. Heterocycl. Comp. 1983, 3, 353-355.
  • Sucman N., Radul O., Pogrebnoi S., Viher V., Gdaniec M., Simonov Iu., Macaev F. The synthesis and the structure of the 1-ethyl-3-(2-oxo-2-phenyletyliden)-2-indolinone, the product of the [2+4]-cycloaddition.All-Russian conference with international participation “Chemistry and Medicine”. 2010. Ufa: Russian Academy of Sciences. p. 317.
  • Macaev F., Ribkovskaia Z., Pogrebnoi S., Boldescu V., Rusu G., Shvets N., Dimoglo A., Geronikaki A., Reynolds R. The structure-antituberculosis activity relationships study in a series of 5-aryl-2-thio-1,3,4-oxadiazole derivatives. Bioorganic and Medicinal Chemistry. 2011, 19, 6792-6807.
  • Macaev F., Rusu G., Pogrebnoi S., Gudima A., Stingaci E., Vlad L., Shvets N., Kandemirli F., Dimoglo A., Reynolds R. Synthesis of Novel 5-Aryl-2-thio-1,3,4-Oxadiazoles and its Structure-Anti-mycobacterial Activity study. Bioorganic and Medicinal Chemistry. 2005, 13, 4842-4850.
  • Geronikaki A., Babaev E., Dearden J., Dehaen W., Filimonov D., Galaeva I., Krajneva V., Lagunin A., Macaev F., Molodavkin G., Poroikov V., Pogrebnoi S., Saloutin V., Stepanchikova A., Stingaci E., Tkach N., Vlad L., Voronina T. Design, synthesis, computational and biological evaluation of new anxiolytics. Bioorganic and Medicinal Chemistry. 2004, 12, 6559-6568.
  • Geronikaki A., Dearden J., Filimonov D., Galaeva I., Garibova T., Gloriozova T., Krajneva V., Lagunin A., Macaev F., Molodavkin G., Poroikov V., Pogrebnoi S., Shepeli F., Voronina T., Tsitlakidou M., Vlad L. Design of new cognition enhancers: from computer prediction to synthesis and biological evaluation. J. Med. Chem. 2004, 47, 2870-2876.
  • MacaevF., RadulO., ShterbetI., PogrebnoiS., SucmanN., MalinovskiiS., BarbaA., Gdaniec M.. Synthesis and structure of new oxoindoles. Chem. Heterocycl. Comp., 2007, 43(3), 298-305
Year 2019, Volume: 1 Issue: 1, 20 - 23, 01.02.2019

Abstract

References

  • Macaev F., Geronikaki A., Sucman N. Recent application of isatins in synthesis of functionalized spirocyclicoxindoles. Chapter in „Targets in heterocycliic systems. Chemistry and Properties”. Ed. O. A. Attanasi and D. Spinelli. Italian Chemical Society, 2011, nr 15, 294-326.
  • Millemaggi A., Taylor R.J.K.3-Alkenyl-oxindoles: natural products, pharmaceuticals, and recent synthetic advances in tandem/telescoped approaches. Eur. J. Org. Chem. 2010, 24, 4527-4547.
  • HanschC.,Sammes P., Taylor J. Comprehensive Medicinal Chemistry. Oxford: Pergamon, 1990. vol. 6. 756 p.
  • Radul O., Junghietu G., Rehter M. Buhaniuk S.A simple way to obtain 1-substituted isatins. Chem. Heterocycl. Comp. 1983, 3, 353-355.
  • Sucman N., Radul O., Pogrebnoi S., Viher V., Gdaniec M., Simonov Iu., Macaev F. The synthesis and the structure of the 1-ethyl-3-(2-oxo-2-phenyletyliden)-2-indolinone, the product of the [2+4]-cycloaddition.All-Russian conference with international participation “Chemistry and Medicine”. 2010. Ufa: Russian Academy of Sciences. p. 317.
  • Macaev F., Ribkovskaia Z., Pogrebnoi S., Boldescu V., Rusu G., Shvets N., Dimoglo A., Geronikaki A., Reynolds R. The structure-antituberculosis activity relationships study in a series of 5-aryl-2-thio-1,3,4-oxadiazole derivatives. Bioorganic and Medicinal Chemistry. 2011, 19, 6792-6807.
  • Macaev F., Rusu G., Pogrebnoi S., Gudima A., Stingaci E., Vlad L., Shvets N., Kandemirli F., Dimoglo A., Reynolds R. Synthesis of Novel 5-Aryl-2-thio-1,3,4-Oxadiazoles and its Structure-Anti-mycobacterial Activity study. Bioorganic and Medicinal Chemistry. 2005, 13, 4842-4850.
  • Geronikaki A., Babaev E., Dearden J., Dehaen W., Filimonov D., Galaeva I., Krajneva V., Lagunin A., Macaev F., Molodavkin G., Poroikov V., Pogrebnoi S., Saloutin V., Stepanchikova A., Stingaci E., Tkach N., Vlad L., Voronina T. Design, synthesis, computational and biological evaluation of new anxiolytics. Bioorganic and Medicinal Chemistry. 2004, 12, 6559-6568.
  • Geronikaki A., Dearden J., Filimonov D., Galaeva I., Garibova T., Gloriozova T., Krajneva V., Lagunin A., Macaev F., Molodavkin G., Poroikov V., Pogrebnoi S., Shepeli F., Voronina T., Tsitlakidou M., Vlad L. Design of new cognition enhancers: from computer prediction to synthesis and biological evaluation. J. Med. Chem. 2004, 47, 2870-2876.
  • MacaevF., RadulO., ShterbetI., PogrebnoiS., SucmanN., MalinovskiiS., BarbaA., Gdaniec M.. Synthesis and structure of new oxoindoles. Chem. Heterocycl. Comp., 2007, 43(3), 298-305

Details

Primary Language English
Subjects Botany, Agricultural Engineering, Agricultural, Veterinary and Food Sciences, Horticultural Production, Agricultural Policy
Journal Section Articles
Authors

Natalia SUCMAN This is me

Vsevolod POGREBNO This is me

Veceslav BOLDESCU This is me

Fliur MACAEV This is me

Publication Date February 1, 2019
Submission Date December 10, 2018
Published in Issue Year 2019 Volume: 1 Issue: 1

Cite

APA SUCMAN, N., POGREBNO, V., BOLDESCU, V., MACAEV, F. (2019). Diastereoselective Synthesis of 3,4-Dıbenzoil-3,4-Dihydro-1H-Spiro [Benzo[cd]Indol-5,3’-Indoline]-2,2’(2aH)-Diones. Uluslararası Anadolu Ziraat Mühendisliği Bilimleri Dergisi, 1(1), 20-23.