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SYNTHESES OF NEW POLYSUBSTITUED DIHYDROFURANS MEDIATED BY MANGANESE III ACETATE

Year 2018, Volume: 60 Issue: 1, 17 - 24, 01.06.2018
https://doi.org/10.1501/commub_0000000557

Abstract

Efficient syntheses of new 4- hydroxymethyl -5,5-dimethyl-2- thiophen2-yl -4,5-dihydrofuran-3-carbonitrile 3a and 4- hydroxymethyl -5,5-dimethyl-2- phenyl-4,5-dihydrofuran-3-carbonitrile 3b were achieved via oxidative addition and cyclization reaction of 3-oxo-3- thiophen-2-yl propanenitrile 1a and 3-oxo-3- phenylpropanenitrile 1b with 3-methylbut-2-en-1-ol 2a in the presence of manganese III acetate. The structures of the compounds 3a and 3b were determined on the basis of spectral data IR, NMR and MS . All spectral data are in good agreement with the proposed structures of compounds.

References

  • M. Mondal and U. Bora, Recent advances in manganese(III) acetate mediated organic synthesis. RSC Advances, 3 (2013) 18716-18754
  • D. Ergüntürk, M. B. Gürdere, Y. Budak and M. Ceylan, Synthesis, characterization, and investigations of antimicrobial activity of 6,6-dimethyl-3- aryl-3′,4′,6,7-tetrahydro-1′H,3H-spiro[benzofuran-2,2′-naphthalene]-1′,4(5H)- dione. Synthetic Communications, 47/16 (2017) 1501–1506.
  • A. S. Demir, and M. Emrullahoğlu, Manganese(III) acetate: A versatile reagent in organic chemistry. Current Organic Synthesis, 4/3 (2007) 223-237.
  • H. Nishino, Manganese(III)-based peroxidation of alkenes to heterocycles. Springer: Berlin, 6 (2006) 39-76.
  • H. Aslan, D. A. Akpınar, A. Öktemer, M. Yakut, and A. Alagöz, Synthesis of dihydropyrans and dihydrofurans via radical cyclization of unsaturated alcohols and 1,3-dicarbonyl compounds. Helvetica Chimica Acta, 97/5 (2014) 652-663.
  • G. Bar, A. F. Parsons, and B. Thomas, Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids. Tetrahedron, 57/22 (2001) 4719-4728.
  • H. Nishino, R. Kumabe, R. Hamada, and M. Yakut, Mn(III)-based reaction of alkenes with quinolinones. Formation of peroxyquinolinones and quinoline- related derivatives. Tetrahedron, 70/7 (2014) 1437-1450.
  • M. Yılmaz, E. V. Burgaz, M. Yakut, and E. Biçer, Synthesis of 4,5-dihydrofuran- 3-carbonitrile derivatives with electron-rich alkenes in the presence of manganese(III) acetate. Journal of the Chinese Chemical Society, 61/10 (2014) 1101-1107.
  • M. Yılmaz, M. Yakut, and A. T. Pekel, Synthesis of 2,3-dihydro-4H-furo[3,2- c]chromen-4-ones and 2,3-dihydronaphtho[2,3-b]furan-4,9-diones by the radical cyclizations of hydroxyenones with electron rich alkenes using manganese(III) acetate. Synthetic Communications, 38/6 (2008) 914-927.
  • H. Aslan, A. Oktemer, H. Dal, and T. Hokelek, Synthesis of ferrocene substituted dihydrofuran derivatives via manganese(III) acetate mediated radical addition- cyclization reactions. Tetrahedron, 73/51 (2017) 7223-7232.
  • M. Yilmaz, N. Uzunalioglu, M. Yakut, and A.T. Pekel, Oxidative cyclizations of 3-oxopropanenitriles substituted alkenes. Turkish Journal of Chemistry, 32/4 (2008) 411-422.
  • M. Özgür, M. Yılmaz and A. T. Pekel, Manganese(III) acetate mediated synthesis of new angular and linear dihydrofuroquinolinones. Communications Faculty of Science University of Ankara Series B, 59/1.2 (2017) 1-11.
  • R. Çalışkan, N. Nohut, Ö. Yılmaz, E. Sahin, and M. Balci, Unusual manganese(III)-mediated oxidative free-radical additions of Meldrum's acid and dimethyl malonate to benzonorbornadiene and oxabenzonorbornadiene. Tetrahedron, 73/4 (2017) 291-297.
  • O. Alagöz, M. Yılmaz, A. T. Pekel, C. Graiff, and R. Maggi, Synthesis of dihydrofuro- and C-alkenylated naphthoquinones catalyzed by manganese(III) acetate, RSC Advances, 4 (2014) 14644.
  • E. Loğoğlu, M. Yılmaz, H. Katircioğlu, M. Yakut, and S. Mercan, Synthesis and biological activity studies of furan derivatives. Medicinal Chemistry Research, 19/5 (2010) 490-497.
  • E. Sarı, H. Aslan, Ş. Dadı, A. Öktemer, E. Loğoğlu, Biological activity studies of some synthesized novel furan and pyran derivatives. Gazi University Journal of Science, 30/4 (2017) 49-55.
  • A. Güvenç, A. T. Pekel, and M. Koçkar, The experimental optimization of the electrosynthesis of manganese(III) acetate in a bipolar packed-bed reactor. Chemical Engineering Journal, 99/3 (2004) 257-263.
  • E. V. Burgaz, M. Yılmaz, and A. Oktemer, Radical cyclizations of conjugated esters and amides with 3-oxopropanenitriles mediated by manganese(III) acetate. ARKIVOC, ii (2011) 363-376.

SYNTHESES OF NEW POLYSUBSTITUED DIHYDROFURANS MEDIATED BY MANGANESE III ACETATE

Year 2018, Volume: 60 Issue: 1, 17 - 24, 01.06.2018
https://doi.org/10.1501/commub_0000000557

Abstract

References

  • M. Mondal and U. Bora, Recent advances in manganese(III) acetate mediated organic synthesis. RSC Advances, 3 (2013) 18716-18754
  • D. Ergüntürk, M. B. Gürdere, Y. Budak and M. Ceylan, Synthesis, characterization, and investigations of antimicrobial activity of 6,6-dimethyl-3- aryl-3′,4′,6,7-tetrahydro-1′H,3H-spiro[benzofuran-2,2′-naphthalene]-1′,4(5H)- dione. Synthetic Communications, 47/16 (2017) 1501–1506.
  • A. S. Demir, and M. Emrullahoğlu, Manganese(III) acetate: A versatile reagent in organic chemistry. Current Organic Synthesis, 4/3 (2007) 223-237.
  • H. Nishino, Manganese(III)-based peroxidation of alkenes to heterocycles. Springer: Berlin, 6 (2006) 39-76.
  • H. Aslan, D. A. Akpınar, A. Öktemer, M. Yakut, and A. Alagöz, Synthesis of dihydropyrans and dihydrofurans via radical cyclization of unsaturated alcohols and 1,3-dicarbonyl compounds. Helvetica Chimica Acta, 97/5 (2014) 652-663.
  • G. Bar, A. F. Parsons, and B. Thomas, Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids. Tetrahedron, 57/22 (2001) 4719-4728.
  • H. Nishino, R. Kumabe, R. Hamada, and M. Yakut, Mn(III)-based reaction of alkenes with quinolinones. Formation of peroxyquinolinones and quinoline- related derivatives. Tetrahedron, 70/7 (2014) 1437-1450.
  • M. Yılmaz, E. V. Burgaz, M. Yakut, and E. Biçer, Synthesis of 4,5-dihydrofuran- 3-carbonitrile derivatives with electron-rich alkenes in the presence of manganese(III) acetate. Journal of the Chinese Chemical Society, 61/10 (2014) 1101-1107.
  • M. Yılmaz, M. Yakut, and A. T. Pekel, Synthesis of 2,3-dihydro-4H-furo[3,2- c]chromen-4-ones and 2,3-dihydronaphtho[2,3-b]furan-4,9-diones by the radical cyclizations of hydroxyenones with electron rich alkenes using manganese(III) acetate. Synthetic Communications, 38/6 (2008) 914-927.
  • H. Aslan, A. Oktemer, H. Dal, and T. Hokelek, Synthesis of ferrocene substituted dihydrofuran derivatives via manganese(III) acetate mediated radical addition- cyclization reactions. Tetrahedron, 73/51 (2017) 7223-7232.
  • M. Yilmaz, N. Uzunalioglu, M. Yakut, and A.T. Pekel, Oxidative cyclizations of 3-oxopropanenitriles substituted alkenes. Turkish Journal of Chemistry, 32/4 (2008) 411-422.
  • M. Özgür, M. Yılmaz and A. T. Pekel, Manganese(III) acetate mediated synthesis of new angular and linear dihydrofuroquinolinones. Communications Faculty of Science University of Ankara Series B, 59/1.2 (2017) 1-11.
  • R. Çalışkan, N. Nohut, Ö. Yılmaz, E. Sahin, and M. Balci, Unusual manganese(III)-mediated oxidative free-radical additions of Meldrum's acid and dimethyl malonate to benzonorbornadiene and oxabenzonorbornadiene. Tetrahedron, 73/4 (2017) 291-297.
  • O. Alagöz, M. Yılmaz, A. T. Pekel, C. Graiff, and R. Maggi, Synthesis of dihydrofuro- and C-alkenylated naphthoquinones catalyzed by manganese(III) acetate, RSC Advances, 4 (2014) 14644.
  • E. Loğoğlu, M. Yılmaz, H. Katircioğlu, M. Yakut, and S. Mercan, Synthesis and biological activity studies of furan derivatives. Medicinal Chemistry Research, 19/5 (2010) 490-497.
  • E. Sarı, H. Aslan, Ş. Dadı, A. Öktemer, E. Loğoğlu, Biological activity studies of some synthesized novel furan and pyran derivatives. Gazi University Journal of Science, 30/4 (2017) 49-55.
  • A. Güvenç, A. T. Pekel, and M. Koçkar, The experimental optimization of the electrosynthesis of manganese(III) acetate in a bipolar packed-bed reactor. Chemical Engineering Journal, 99/3 (2004) 257-263.
  • E. V. Burgaz, M. Yılmaz, and A. Oktemer, Radical cyclizations of conjugated esters and amides with 3-oxopropanenitriles mediated by manganese(III) acetate. ARKIVOC, ii (2011) 363-376.
There are 18 citations in total.

Details

Primary Language Turkish
Journal Section Research Article
Authors

Hakan Aslan This is me

Fatma Eroğlu This is me

Mehtap Özgür This is me

Publication Date June 1, 2018
Published in Issue Year 2018 Volume: 60 Issue: 1

Cite

Vancouver Aslan H, Eroğlu F, Özgür M. SYNTHESES OF NEW POLYSUBSTITUED DIHYDROFURANS MEDIATED BY MANGANESE III ACETATE. Commun. Fac. Sci. Univ. Ank. Ser. B. 2018;60(1):17-24.

Communications Faculty of Sciences University of Ankara Series B Chemistry and Chemical Engineering

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