BibTex RIS Cite

MANGANESE III ACETATE MEDIATED SYNTHESIS OF NEW ANGULAR AND LINEAR DIHYDROFUROQUINOLINONES

Year 2017, Volume: 59 Issue: 1.2, 1 - 11, 01.06.2017
https://doi.org/10.1501/commub_0000000555

Abstract

Angular 3 and linear 4 dihydrofuroquinolinone derivatives were prepared in ‘one pot’ reaction of 4-hydroxy-1-methyl-quinoline-2-one 1 with E -2- 1-phenylprop-1-en-2-yl thiophene 2 in the presence of manganese III acetate. The structures of the compounds 3 and 4 were determined by MS, FTIR, ID and 2D NMR techniques. A possible reaction mechanism was also described.

References

  • [1] J. P. Michael, Quinoline, quinazoline and accordion alkaloids. Natural Product Reports, 21/5 (2004) 650-668.
  • [2] J. P. Michael, Quinoline, quinazoline and accordion alkaloids. Natural Product Reports, 25/1 (2008) 166-187.
  • [3] R. Naik, M.V Kulkarni, A. Kumar, and T.N. Guru Row, One pot three component diastereoselective synthesis of tricyclic furoquinolones and furocoumarins. Modern Organic Chemistry Research, 2/4 (2017), 179-188.
  • [4] J. Su , J. Xiong , S. Liang , G. Qiu , X. Feng , H. Teng , L. Wu, and X. Hu, Concise synthesis of the angular dihydrofuroquinoline alkaloids via cyclopropane opening in the presence of polyphosphoric acid. Synthetic Communications, 36/6 (2006) 693-699.
  • [5] A. Ustalar, M. Yılmaz, A. Osmani, and S.A.Keçeli, Synthesis and antifungal activity of new dihydrofurocoumarins and dihydrofuroquinolines. Turkish Journal of Chemistry, 41/1 (2017), 80-88.
  • [6] 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.
  • [7] H. Nishino, R. Kumabe, R. Hamada, and M. Yakut, Mn(III)-based reaction of alkenes with quinolinones. Formation of peroxyquinolinones and quinolinerelated derivatives. Tetrahedron, 70/7 (2014) 1437-1450.
  • [8] H. Nishino, Manganese(III)-Based Peroxidation of Alkenes to Heterocycles. Springer: Berlin, 6 (2006) 39-76.
  • [9] A. S. Demir, and M. Emrullahoğlu, Manganese(III) acetate: A versatile reagent in organic chemistry. Current Organic Synthesis, 4/3 (2007) 223-237.
  • [10] 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.
  • [11] G. Bar, A.F. Parsons, and B. Thomas, A radical approach to araliopsine and related quinoline alkaloids using manganese(III) acetate. Tetrahedron Letters, 41/40 (2000) 7751-7755.
  • [12] M. Yılmaz, E.V. Burgaz, M. Yakut, and E. Biçer, Synthesis of 4,5-dihydrofuran3-carbonitrile derivatives with electron-rich alkenes in the presence of manganese(III) acetate. Journal of the Chineese Chemical Society, 61/10 (2014) 1101-1107.
  • [13] M. Yılmaz, Synthesis of dihydrofurans containing trifluoromethyl ketone and heterocycles by radical cyclization of fluorinated 1,3-dicarbonyl compounds with 2-thienyl and 2-furyl substituted alkenes. Tetrahedron, 67/43 (2011) 8255-8263.
  • [14] 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.
  • [15] 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.
  • [16] 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.
  • [17] 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.
  • [18] M. Yilmaz, N. Uzunalioglu, M. Yakut, and AT. Pekel, Oxidative cyclizations of 3-oxopropanenitriles mediated manganese(III) acetate with 2-thienyl substituted alkenes. Turkish Jornal of Chemistry, 32/4 (2008) 411-422.

MANGANESE III ACETATE MEDIATED SYNTHESIS OF NEW ANGULAR AND LINEAR DIHYDROFUROQUINOLINONES

Year 2017, Volume: 59 Issue: 1.2, 1 - 11, 01.06.2017
https://doi.org/10.1501/commub_0000000555

Abstract

References

  • [1] J. P. Michael, Quinoline, quinazoline and accordion alkaloids. Natural Product Reports, 21/5 (2004) 650-668.
  • [2] J. P. Michael, Quinoline, quinazoline and accordion alkaloids. Natural Product Reports, 25/1 (2008) 166-187.
  • [3] R. Naik, M.V Kulkarni, A. Kumar, and T.N. Guru Row, One pot three component diastereoselective synthesis of tricyclic furoquinolones and furocoumarins. Modern Organic Chemistry Research, 2/4 (2017), 179-188.
  • [4] J. Su , J. Xiong , S. Liang , G. Qiu , X. Feng , H. Teng , L. Wu, and X. Hu, Concise synthesis of the angular dihydrofuroquinoline alkaloids via cyclopropane opening in the presence of polyphosphoric acid. Synthetic Communications, 36/6 (2006) 693-699.
  • [5] A. Ustalar, M. Yılmaz, A. Osmani, and S.A.Keçeli, Synthesis and antifungal activity of new dihydrofurocoumarins and dihydrofuroquinolines. Turkish Journal of Chemistry, 41/1 (2017), 80-88.
  • [6] 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.
  • [7] H. Nishino, R. Kumabe, R. Hamada, and M. Yakut, Mn(III)-based reaction of alkenes with quinolinones. Formation of peroxyquinolinones and quinolinerelated derivatives. Tetrahedron, 70/7 (2014) 1437-1450.
  • [8] H. Nishino, Manganese(III)-Based Peroxidation of Alkenes to Heterocycles. Springer: Berlin, 6 (2006) 39-76.
  • [9] A. S. Demir, and M. Emrullahoğlu, Manganese(III) acetate: A versatile reagent in organic chemistry. Current Organic Synthesis, 4/3 (2007) 223-237.
  • [10] 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.
  • [11] G. Bar, A.F. Parsons, and B. Thomas, A radical approach to araliopsine and related quinoline alkaloids using manganese(III) acetate. Tetrahedron Letters, 41/40 (2000) 7751-7755.
  • [12] M. Yılmaz, E.V. Burgaz, M. Yakut, and E. Biçer, Synthesis of 4,5-dihydrofuran3-carbonitrile derivatives with electron-rich alkenes in the presence of manganese(III) acetate. Journal of the Chineese Chemical Society, 61/10 (2014) 1101-1107.
  • [13] M. Yılmaz, Synthesis of dihydrofurans containing trifluoromethyl ketone and heterocycles by radical cyclization of fluorinated 1,3-dicarbonyl compounds with 2-thienyl and 2-furyl substituted alkenes. Tetrahedron, 67/43 (2011) 8255-8263.
  • [14] 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.
  • [15] 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.
  • [16] 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.
  • [17] 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.
  • [18] M. Yilmaz, N. Uzunalioglu, M. Yakut, and AT. Pekel, Oxidative cyclizations of 3-oxopropanenitriles mediated manganese(III) acetate with 2-thienyl substituted alkenes. Turkish Jornal of Chemistry, 32/4 (2008) 411-422.
There are 18 citations in total.

Details

Primary Language English
Journal Section Research Article
Authors

Mehtap Özgür This is me

Mehmet Yılmaz This is me

A.tarık Pekel This is me

Publication Date June 1, 2017
Published in Issue Year 2017 Volume: 59 Issue: 1.2

Cite

Vancouver Özgür M, Yılmaz M, Pekel A. MANGANESE III ACETATE MEDIATED SYNTHESIS OF NEW ANGULAR AND LINEAR DIHYDROFUROQUINOLINONES. Commun. Fac. Sci. Univ. Ank. Ser. B. 2017;59(1.2):1-11.

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

Creative Commons License

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