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SYNTHESES OF NEW POLYSUBSTITUED DIHYDROFURANS MEDIATED BY MANGANESE III ACETATE

Yıl 2018, Cilt: 60 Sayı: 1, 17 - 24, 01.06.2018
https://doi.org/10.1501/commub_0000000557

Öz

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.

Kaynakça

  • 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

Yıl 2018, Cilt: 60 Sayı: 1, 17 - 24, 01.06.2018
https://doi.org/10.1501/commub_0000000557

Öz

Kaynakça

  • 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.
Toplam 18 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Bölüm Research Article
Yazarlar

Hakan Aslan Bu kişi benim

Fatma Eroğlu Bu kişi benim

Mehtap Özgür Bu kişi benim

Yayımlanma Tarihi 1 Haziran 2018
Yayımlandığı Sayı Yıl 2018 Cilt: 60 Sayı: 1

Kaynak Göster

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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This work is licensed under a Creative Commons Attribution 4.0 International License.