MANGANESE III ACETATE MEDIATED SYNTHESIS OF NEW ANGULAR AND LINEAR DIHYDROFUROQUINOLINONES
Year 2017,
Volume: 59 Issue: 1.2, 1 - 11, 01.06.2017
Mehtap Özgür
Mehmet Yılmaz
A.tarık Pekel
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.
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MANGANESE III ACETATE MEDIATED SYNTHESIS OF NEW ANGULAR AND LINEAR DIHYDROFUROQUINOLINONES
Year 2017,
Volume: 59 Issue: 1.2, 1 - 11, 01.06.2017
Mehtap Özgür
Mehmet Yılmaz
A.tarık Pekel
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.