Synthesis of new 4,6-diaryl-2-(arylthio)nicotinonitriles in Triton X-100 aqueous micellar media

Mohammad Reza Poor Heravi Amir Soufi

Citation:  Mohammad Reza Poor Heravi, Amir Soufi. Synthesis of new 4,6-diaryl-2-(arylthio)nicotinonitriles in Triton X-100 aqueous micellar media[J]. Chinese Chemical Letters, 2015, 26(2): 263-266. doi: 10.1016/j.cclet.2014.11.007 shu

Synthesis of new 4,6-diaryl-2-(arylthio)nicotinonitriles in Triton X-100 aqueous micellar media

    通讯作者: Mohammad Reza Poor Heravi,
摘要: In this communication, we report four component condensations of acetophenone, arylaldehydes, arylthiol, and malononitrile in the presence of Triton X-100 (5 mol%) aqueous micelles. This reaction led to the formation of 4,6-diaryl-2-(arylthio)nicotinonitrile new derivatives in good yields. The FT-IR, 19F NMR, 1H NMR, 13C NMR spectra and elemental analysis confirm the structure of compounds.

English

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    1. [1] H. Mitsuya, R. Yarchoan, S. Broder, Molecular targets for AIDS therapy, Science 249 (1990) 1533-1544.[1] H. Mitsuya, R. Yarchoan, S. Broder, Molecular targets for AIDS therapy, Science 249 (1990) 1533-1544.

    2. [2] J.A. Montgomery, Approaches to antiviral chemotherapy, Antiviral Res. 12 (1989) 113-132.[2] J.A. Montgomery, Approaches to antiviral chemotherapy, Antiviral Res. 12 (1989) 113-132.

    3. [3] X. Zhang, D. Li, X. Fan, et al., Ionic liquid-promoted multi-component reaction: novel and efficient preparation of pyrazolo[3, 4-b]pyridinone, pyrazolo[3,4-b]-quinolinone and their hybrids with pyrimidine nucleoside, Mol. Divers 14 (2010) 159-167.[3] X. Zhang, D. Li, X. Fan, et al., Ionic liquid-promoted multi-component reaction: novel and efficient preparation of pyrazolo[3, 4-b]pyridinone, pyrazolo[3,4-b]-quinolinone and their hybrids with pyrimidine nucleoside, Mol. Divers 14 (2010) 159-167.

    4. [4] O.M. Ahmed, M.A. Mohamed, R.R. Ahmed, S.A. Ahmed, Synthesis and anti-tumor activities of some new pyridines and pyrazolo[1, 5-a]pyrimidines, Eur. J. Med. Chem. 44 (2009) 3519-3523.[4] O.M. Ahmed, M.A. Mohamed, R.R. Ahmed, S.A. Ahmed, Synthesis and anti-tumor activities of some new pyridines and pyrazolo[1, 5-a]pyrimidines, Eur. J. Med. Chem. 44 (2009) 3519-3523.

    5. [5] M.G. Mamolo, D. Zampieri, V. Falagiani, L. Vio, E. Banfi, Synthesis and antimycobacterial activity of 5-aryl-1-isonicotinoyl-3-(pyridin-2-yl)-4, 5-dihydro-1H-pyrazole derivatives, II Farmaco 56 (2001) 593-599.[5] M.G. Mamolo, D. Zampieri, V. Falagiani, L. Vio, E. Banfi, Synthesis and antimycobacterial activity of 5-aryl-1-isonicotinoyl-3-(pyridin-2-yl)-4, 5-dihydro-1H-pyrazole derivatives, II Farmaco 56 (2001) 593-599.

    6. [6] C.O. Badgett, C.F. Woodward, Nicotinic acid, miscellaneous esters, J. Am. Chem. Soc. 69 (1947), 2907-2907.[6] C.O. Badgett, C.F. Woodward, Nicotinic acid, miscellaneous esters, J. Am. Chem. Soc. 69 (1947), 2907-2907.

    7. [7] R. Gupta, A. Jain, M. Jain, R. Joshi, ‘One pot’synthesis of 2-amino-3-cyano-4,6-diarylpyridines under ultrasonic irradiation and grindstone technology, Bull, Korean Chem. Soc. 31 (2010) 3180-3182.[7] R. Gupta, A. Jain, M. Jain, R. Joshi, ‘One pot’synthesis of 2-amino-3-cyano-4,6-diarylpyridines under ultrasonic irradiation and grindstone technology, Bull, Korean Chem. Soc. 31 (2010) 3180-3182.

    8. [8] G. Dorner, F.W. Fischer, On the modification of serum lipids and lipoproteins by the hexanicotinic acid ester of m-inositol, Arzenmittel. Forsch. 11 (1961) 110-113.[8] G. Dorner, F.W. Fischer, On the modification of serum lipids and lipoproteins by the hexanicotinic acid ester of m-inositol, Arzenmittel. Forsch. 11 (1961) 110-113.

    9. [9] V.K. Indirapriyadharshini, P. Ramamurthy, V. Raghukumar, V.T. Ramakrishma, Spectral and photophysical properties of 1,6-naphthyridine derivatives: a new class of compounds for nonlinear optics, Spectrochim. Acta A 58 (2002) 1535-1543.[9] V.K. Indirapriyadharshini, P. Ramamurthy, V. Raghukumar, V.T. Ramakrishma, Spectral and photophysical properties of 1,6-naphthyridine derivatives: a new class of compounds for nonlinear optics, Spectrochim. Acta A 58 (2002) 1535-1543.

    10. [10] T.J. Meyer, Chemical approach to artificial photosynthesis, J. Acc. Chem. Res. 22 (1989) 163-170.[10] T.J. Meyer, Chemical approach to artificial photosynthesis, J. Acc. Chem. Res. 22 (1989) 163-170.

    11. [11] G.S. Hanan, D. Volmer, U.S. Schubert, et al., Coordination arrays: tetranuclear cobalt(II) complexes with [2 2]-Grid structure, Angew. Chem., Int. Ed. 36 (1997) 1842-1844.[11] G.S. Hanan, D. Volmer, U.S. Schubert, et al., Coordination arrays: tetranuclear cobalt(II) complexes with [2 2]-Grid structure, Angew. Chem., Int. Ed. 36 (1997) 1842-1844.

    12. [12] A.I. Pavluchenko, V.F. Petrov, N.I. Simirnova, Liquid crystalline 2,5-disubstituted pyridine derivatives, Liq. Cryst. 19 (1995) 811-821.[12] A.I. Pavluchenko, V.F. Petrov, N.I. Simirnova, Liquid crystalline 2,5-disubstituted pyridine derivatives, Liq. Cryst. 19 (1995) 811-821.

    13. [13] (a) G.R. Pabst, J. Sauer, A new and simple ‘LEGO’ system for the synthesis of 2,6-oligopyridines, Tetrahedron Lett. 39 (1998) 6687-6690; (b) G.R. Pabst, O.C. Pfuller, J. Sauer, The new and simple ‘LEGO’system: synthesis and reactions of ruthenium (II) complexes, Tetrahedron Lett. 39 (1998) 8825-8828.[13] (a) G.R. Pabst, J. Sauer, A new and simple ‘LEGO’ system for the synthesis of 2,6-oligopyridines, Tetrahedron Lett. 39 (1998) 6687-6690; (b) G.R. Pabst, O.C. Pfuller, J. Sauer, The new and simple ‘LEGO’system: synthesis and reactions of ruthenium (II) complexes, Tetrahedron Lett. 39 (1998) 8825-8828.

    14. [14] A. Alberola, L.A. Calvo, A.G. Ortega, R.M.C. Sanudo, P. Yustos, Regioselective synthesis of 2(1H)-pyridinones from b-aminoenones and malononitrile reaction mechanism, J. Org. Chem. 64 (1999) 9493-9498.[14] A. Alberola, L.A. Calvo, A.G. Ortega, R.M.C. Sanudo, P. Yustos, Regioselective synthesis of 2(1H)-pyridinones from b-aminoenones and malononitrile reaction mechanism, J. Org. Chem. 64 (1999) 9493-9498.

    15. [15] N.M. Evdokimov, I.V. Magedov, A.S. Kireev, A. Komienko, One-step, three-component synthesis of pyridines and 1,4-dihydropyridines with manifold medicinal utility, Org. Lett. 8 (2006) 899-902.[15] N.M. Evdokimov, I.V. Magedov, A.S. Kireev, A. Komienko, One-step, three-component synthesis of pyridines and 1,4-dihydropyridines with manifold medicinal utility, Org. Lett. 8 (2006) 899-902.

    16. [16] A.W. Fatland, B.E. Eaton, Cobalt-catalyzed alkyne-nitrile cyclotrimerization to form pyridines in aqueous solution, Org. Lett. 2 (2000) 3131-3133.[16] A.W. Fatland, B.E. Eaton, Cobalt-catalyzed alkyne-nitrile cyclotrimerization to form pyridines in aqueous solution, Org. Lett. 2 (2000) 3131-3133.

    17. [17] M.R. Poor Heravi, F. Fakhr, Ultrasound-promoted synthesis of 2-amino-6-(arylthio)-4-arylpyridine-3, 5-dicarbonitriles using ZrOCl2 8H2O as the catalyst in the ionic liquid [bmim]BF4 at room temperature, Tetrahedron Lett. 52 (2011) 6779-6782.[17] M.R. Poor Heravi, F. Fakhr, Ultrasound-promoted synthesis of 2-amino-6-(arylthio)-4-arylpyridine-3, 5-dicarbonitriles using ZrOCl2 8H2O as the catalyst in the ionic liquid [bmim]BF4 at room temperature, Tetrahedron Lett. 52 (2011) 6779-6782.

    18. [18] X.M. Rimaz, H. Mousavi, A one-pot strategy for regioselective synthesis of 6-aryl-3-oxo-2, 3-dihydropyridazine-4-carbohydrazides, Turk. J. Chem. 37 (2013) 252-261.[18] X.M. Rimaz, H. Mousavi, A one-pot strategy for regioselective synthesis of 6-aryl-3-oxo-2, 3-dihydropyridazine-4-carbohydrazides, Turk. J. Chem. 37 (2013) 252-261.

    19. [19] R.C.F. Jones, M.J. Smallridge, Annulation of imidazolines: synthesis of imidazo [1, 2-a] pyridones, Tetrahedron Lett. 29 (1988) 5005-5008.[19] R.C.F. Jones, M.J. Smallridge, Annulation of imidazolines: synthesis of imidazo [1, 2-a] pyridones, Tetrahedron Lett. 29 (1988) 5005-5008.

    20. [20] M.N. Jones, Two-dimensional electrophoresis of membrane proteins using immobilized pH gradients, Int. J. Pharm. 177 (1999) 137-139.[20] M.N. Jones, Two-dimensional electrophoresis of membrane proteins using immobilized pH gradients, Int. J. Pharm. 177 (1999) 137-139.

    21. [21] X. Zeng, K. Osseo-Asare, Partitioning behavior of silica in the Triton X-100/ dextran/water aqueous biphasic system, J. Colloid Interface Sci. 272 (2004) 298-307.[21] X. Zeng, K. Osseo-Asare, Partitioning behavior of silica in the Triton X-100/ dextran/water aqueous biphasic system, J. Colloid Interface Sci. 272 (2004) 298-307.

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  • 发布日期:  2014-11-11
  • 收稿日期:  2014-06-23
  • 网络出版日期:  2014-10-27
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