A green multicomponent synthesis of bioactive pyrimido[4, 5-b]quinoline derivatives as antibacterial agents in water catalyzed by RuCl3·xH2O

Khalil Tabatabaeian Abdollah Fallah Shojaei Farhad Shirini Seyyedeh Zoha Hejazi Mehdi Rassa

Citation:  Khalil Tabatabaeian, Abdollah Fallah Shojaei, Farhad Shirini, Seyyedeh Zoha Hejazi, Mehdi Rassa. A green multicomponent synthesis of bioactive pyrimido[4, 5-b]quinoline derivatives as antibacterial agents in water catalyzed by RuCl3·xH2O[J]. Chinese Chemical Letters, 2014, 25(2): 308-312. shu

A green multicomponent synthesis of bioactive pyrimido[4, 5-b]quinoline derivatives as antibacterial agents in water catalyzed by RuCl3·xH2O

    通讯作者: Khalil Tabatabaeian,
摘要: An efficient, convenient and environmentally benign one-pot multicomponent reaction for the preparation of pyrimido[4,5-b]quinoline derivatives as biologically, pharmacologically and antibacterially active products has been developed using RuCl3·xH2O as a reusable homogenous catalyst. Use of water as a green solvent, purification of products by non-chromatographic methods, reusability of transition metal homogenous catalyst, saving energy by employing multicomponent reactions, short reaction times and high yields, are some of the advantages of this process.

English

  • 
    1. [1] P.A. Grieco, Organic Synthesis inWater, Thomson Science, London, 1998, pp. 1-278.[1] P.A. Grieco, Organic Synthesis inWater, Thomson Science, London, 1998, pp. 1-278.

    2. [2] (a) R. Breslow, U. Maitra, On the origin of product selectivity in aqueous Diels- Alder reactions, Tetrahedron Lett. 25 (1984) 1239-1240; (b) D.C. Rideout, R. Breslow, Hydrophobic acceleration of Diels-Alder reactions, J. Am. Chem. Soc. 102 (1980) 7816-7817.[2] (a) R. Breslow, U. Maitra, On the origin of product selectivity in aqueous Diels- Alder reactions, Tetrahedron Lett. 25 (1984) 1239-1240; (b) D.C. Rideout, R. Breslow, Hydrophobic acceleration of Diels-Alder reactions, J. Am. Chem. Soc. 102 (1980) 7816-7817.

    3. [3] S. Narayan, J. Muldoon, M.G. Finn, et al., On water: unique reactivity of organic compounds in aqueous suspension, Angew. Chem. Int. Ed. 44 (2005) 3275-3279.[3] S. Narayan, J. Muldoon, M.G. Finn, et al., On water: unique reactivity of organic compounds in aqueous suspension, Angew. Chem. Int. Ed. 44 (2005) 3275-3279.

    4. [4] B. Sharifzadeh, N.O. Mahmoodi, M. Mamaghani, et al., Facile regioselective synthesis of novel bioactive thiazolyl-pyrazolinederivatives via a three-component reaction and their antimicrobial activity, Bioorg. Med. Chem. Lett. 23 (2013) 548-551.[4] B. Sharifzadeh, N.O. Mahmoodi, M. Mamaghani, et al., Facile regioselective synthesis of novel bioactive thiazolyl-pyrazolinederivatives via a three-component reaction and their antimicrobial activity, Bioorg. Med. Chem. Lett. 23 (2013) 548-551.

    5. [5] R. Hossein nia, M. Mamaghani, K. Tabatabaeian, F. Shirini, M. Rassa, An expeditious regioselective synthesis of novel bioactive indole-substituted chromene derivatives via one-pot three-component reaction, Bioorg. Med. Chem. Lett. 22 (2012) 5956-5960.[5] R. Hossein nia, M. Mamaghani, K. Tabatabaeian, F. Shirini, M. Rassa, An expeditious regioselective synthesis of novel bioactive indole-substituted chromene derivatives via one-pot three-component reaction, Bioorg. Med. Chem. Lett. 22 (2012) 5956-5960.

    6. [6] C.C.A. Cariou, G.J. Clarkson, M.J. Shipman, Rapid synthesis of 1,3,4,4'-tetrasubstituted blactams from methyleneaziridines using a 4-component reaction, Org. Chem. 73 (2008) 9762-9764.[6] C.C.A. Cariou, G.J. Clarkson, M.J. Shipman, Rapid synthesis of 1,3,4,4'-tetrasubstituted blactams from methyleneaziridines using a 4-component reaction, Org. Chem. 73 (2008) 9762-9764.

    7. [7] B.M. Trost, Atom economy. A challenge for organic synthesis, homogeneous catalysis leads the way, Angew. Chem. Int. Ed. Engl. 34 (1995) 259-281.[7] B.M. Trost, Atom economy. A challenge for organic synthesis, homogeneous catalysis leads the way, Angew. Chem. Int. Ed. Engl. 34 (1995) 259-281.

    8. [8] (a) L.F. Tietze, Domino reactions in organic synthesis, Chem. Rev. 96 (1996) 115-136; (b) H. Waldmann, Domino reaction, in: Organic Synthesis Highlight II, VCH, Weinheim, 1995, pp. 193-202.[8] (a) L.F. Tietze, Domino reactions in organic synthesis, Chem. Rev. 96 (1996) 115-136; (b) H. Waldmann, Domino reaction, in: Organic Synthesis Highlight II, VCH, Weinheim, 1995, pp. 193-202.

    9. [9] A.M. Triggle, E. Shefter, D.J. Triggle, Crystal structures of calcium channel antagonists: 2,6-dimethyl-3,5-dicarbomethoxy-4-[2-nitro-3-cyano-4-(dimethylamino)-, and 2,3,4,5,6-pentafluorophenyl]-1,4-dihydropyridine, J. Med. Chem. 23 (1980) 1442-1445.[9] A.M. Triggle, E. Shefter, D.J. Triggle, Crystal structures of calcium channel antagonists: 2,6-dimethyl-3,5-dicarbomethoxy-4-[2-nitro-3-cyano-4-(dimethylamino)-, and 2,3,4,5,6-pentafluorophenyl]-1,4-dihydropyridine, J. Med. Chem. 23 (1980) 1442-1445.

    10. [10] R. Fossheim, K. Svarteng, A. Mostad, et al., Crystal structures and pharmacological activity of calcium channel antagonists: 2,6-dimethyl-3,5-dicarbomethoxy-4- (unsubstituted, 2-methyl-, 4-methyl-, 3-nitro-, 4-nitro-, and 2,4-dinitrophenyl)- 1,4-dihydropyridine, J. Med. Chem. 25 (1982) 126-131.[10] R. Fossheim, K. Svarteng, A. Mostad, et al., Crystal structures and pharmacological activity of calcium channel antagonists: 2,6-dimethyl-3,5-dicarbomethoxy-4- (unsubstituted, 2-methyl-, 4-methyl-, 3-nitro-, 4-nitro-, and 2,4-dinitrophenyl)- 1,4-dihydropyridine, J. Med. Chem. 25 (1982) 126-131.

    11. [11] R.P. Mason, I.T. Mark, M.W. Trumbore, P.E. Masson, Antioxidant properties of calcium antagonists related to membrane biophysical interactions, Am. J. Cardiol. 84 (1999) 16-22.[11] R.P. Mason, I.T. Mark, M.W. Trumbore, P.E. Masson, Antioxidant properties of calcium antagonists related to membrane biophysical interactions, Am. J. Cardiol. 84 (1999) 16-22.

    12. [12] G.K. Verma, K. Raghuvanshi, R. Kumar, M.S. Singh, An efficient one-pot threecomponent synthesis of functionalized pyrimido[4,5-b]quinolines and indeno fused pyrido[2,3-d]pyrimidines in water, Tetrahedron Lett. 53 (2012) 399-402.[12] G.K. Verma, K. Raghuvanshi, R. Kumar, M.S. Singh, An efficient one-pot threecomponent synthesis of functionalized pyrimido[4,5-b]quinolines and indeno fused pyrido[2,3-d]pyrimidines in water, Tetrahedron Lett. 53 (2012) 399-402.

    13. [13] D.Q. Shi, S.N. Ni, F. Yang, et al., An efficient synthesis of pyrimido[4,5-b]quinoline and indeno[20,10:5,6]pyrido[2,3-d]pyrimidine derivatives via multicomponent reactions in ionic liquid, J. Heterocycl. Chem. 45 (2008) 693-702.[13] D.Q. Shi, S.N. Ni, F. Yang, et al., An efficient synthesis of pyrimido[4,5-b]quinoline and indeno[20,10:5,6]pyrido[2,3-d]pyrimidine derivatives via multicomponent reactions in ionic liquid, J. Heterocycl. Chem. 45 (2008) 693-702.

    14. [14] N.A. Hassan, M.I. Hegab, A.I. Hashem, et al., Three-component, one-pot synthesis of pyrimido[4,5-b]-quinoline and pyrido[2,3-d]pyrimidine derivatives, J. Heterocycl. Chem. 44 (2007) 775-782.[14] N.A. Hassan, M.I. Hegab, A.I. Hashem, et al., Three-component, one-pot synthesis of pyrimido[4,5-b]-quinoline and pyrido[2,3-d]pyrimidine derivatives, J. Heterocycl. Chem. 44 (2007) 775-782.

    15. [15] F. Nemati, R. Saeedirad, Nano-Fe3O4 encapsulated-silica particles bearing sulfonic acid groups as a magnetically separable catalyst for green and efficient synthesis of functionalized pyrimido[4,5-b]quinolines and indeno fused pyrido[2,3-d]pyrimidines in water, Chin. Chem. Lett. 24 (2013) 370-372.[15] F. Nemati, R. Saeedirad, Nano-Fe3O4 encapsulated-silica particles bearing sulfonic acid groups as a magnetically separable catalyst for green and efficient synthesis of functionalized pyrimido[4,5-b]quinolines and indeno fused pyrido[2,3-d]pyrimidines in water, Chin. Chem. Lett. 24 (2013) 370-372.

    16. [16] H.Y. Guo, Y. Yu, One-pot synthesis of 7-aryl-11,12-dihydrobenzo[h]pyrimido-[4,5-b]quinoline-8,10(7H,9H)-diones via three-component reaction in ionic liquid, Chin. Chem. Lett. 21 (2010) 1435-1438.[16] H.Y. Guo, Y. Yu, One-pot synthesis of 7-aryl-11,12-dihydrobenzo[h]pyrimido-[4,5-b]quinoline-8,10(7H,9H)-diones via three-component reaction in ionic liquid, Chin. Chem. Lett. 21 (2010) 1435-1438.

    17. [17] Y.S. Sanghhvi, S.B. Larson, S.S. Matsumoto, et al., Antitumor and antiviral activity of synthetic alpha- and beta-ribonucleosides of certain substituted pyrimido[5,4- d]pyrimidines: a new synthetic strategy for exocyclic aminonucleosides, J. Med. Chem. 32 (1989) 629-637.[17] Y.S. Sanghhvi, S.B. Larson, S.S. Matsumoto, et al., Antitumor and antiviral activity of synthetic alpha- and beta-ribonucleosides of certain substituted pyrimido[5,4- d]pyrimidines: a new synthetic strategy for exocyclic aminonucleosides, J. Med. Chem. 32 (1989) 629-637.

    18. [18] R.B. Tenser, A. Gaydos, K.A. Hay, Inhibition of herpes simplex virus reactivation by dipyridamole, Antimicrob. Agents Chemother. 45 (2001) 3657-3659.[18] R.B. Tenser, A. Gaydos, K.A. Hay, Inhibition of herpes simplex virus reactivation by dipyridamole, Antimicrob. Agents Chemother. 45 (2001) 3657-3659.

    19. [19] J.P. De la Cruz, T. Carrasco, G. Ortega, F. Sanchez De la Cuesta, Inhibition of ferrousinduced lipid peroxidation by pyrimido-pyrimidine derivatives in human liver membranes, Lipid 27 (1992) 192-194.[19] J.P. De la Cruz, T. Carrasco, G. Ortega, F. Sanchez De la Cuesta, Inhibition of ferrousinduced lipid peroxidation by pyrimido-pyrimidine derivatives in human liver membranes, Lipid 27 (1992) 192-194.

    20. [20] B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali, N.S. Shetty, Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents, Bioorg. Med. Chem. 14 (2006) 2040-2047.[20] B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali, N.S. Shetty, Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents, Bioorg. Med. Chem. 14 (2006) 2040-2047.

    21. [21] H.C. Aspinall, Chiral lanthanide complexes: coordination chemistry and applications, Chem. Rev. 102 (2002) 1807-1850.[21] H.C. Aspinall, Chiral lanthanide complexes: coordination chemistry and applications, Chem. Rev. 102 (2002) 1807-1850.

    22. [22] H. Yu, M.S. Zhang, L.R. Cui, Copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles from imidoyl chlorides, Chin. Chem. Lett. 23 (2012) 573-575.[22] H. Yu, M.S. Zhang, L.R. Cui, Copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles from imidoyl chlorides, Chin. Chem. Lett. 23 (2012) 573-575.

    23. [23] I. Murahashi, Ruthenium in Organic Synthesis, Wiley-VCH, New York, 2004.[23] I. Murahashi, Ruthenium in Organic Synthesis, Wiley-VCH, New York, 2004.

    24. [24] K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, Efficient RuⅢcatalyzed condensation of indoles and aldehydes or ketones, Can. J. Chem. 84 (2006) 1541-1545.[24] K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, Efficient RuⅢcatalyzed condensation of indoles and aldehydes or ketones, Can. J. Chem. 84 (2006) 1541-1545.

    25. [25] K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, Ultrasonicassisted ruthenium-catalyzed oxidation of aromatic and heteroaromatic compounds, Catal. Commun. 9 (2008) 416-420.[25] K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, Ultrasonicassisted ruthenium-catalyzed oxidation of aromatic and heteroaromatic compounds, Catal. Commun. 9 (2008) 416-420.

    26. [26] K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, RuⅢ-catalyzed double-conjugate 1,4-addition of indoles to symmetric enones, J. Mol. Catal. A: Chem. 270 (2007) 112-116.[26] K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, RuⅢ-catalyzed double-conjugate 1,4-addition of indoles to symmetric enones, J. Mol. Catal. A: Chem. 270 (2007) 112-116.

    27. [27] K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, Solvent-free, ruthenium-catalyzed, regioselective ring-opening of epoxides, an efficient route to various 3-alkylated indoles, Tetrahedron Lett. 49 (2008) 1450-1454.[27] K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, Solvent-free, ruthenium-catalyzed, regioselective ring-opening of epoxides, an efficient route to various 3-alkylated indoles, Tetrahedron Lett. 49 (2008) 1450-1454.

    28. [28] K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, Ruthenium-catalyzed efficient routes to oxindole derivatives, Can. J. Chem. 87 (2009) 1213-1217.[28] K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, Ruthenium-catalyzed efficient routes to oxindole derivatives, Can. J. Chem. 87 (2009) 1213-1217.

    29. [29] K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, Diastereoselective ruthenium-catalyzed Michael addition of indoles to hormone steroids: an efficient route to new indole derivatives, Synth. Commun. 40 (2010) 1677-1684.[29] K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, A. Khorshidi, Diastereoselective ruthenium-catalyzed Michael addition of indoles to hormone steroids: an efficient route to new indole derivatives, Synth. Commun. 40 (2010) 1677-1684.

    30. [30] K. Tabatabaeian, A. Khorshidi, M. Mamaghani, A. Dadashi, M. Khoshnood Jalali, One-pot synthesis of tetrahydrobenzo[a]xanthen-11-one derivatives catalyzed by ruthenium chloride hydrate as a homogeneous catalyst, Can. J. Chem. 89 (2011) 623-627.[30] K. Tabatabaeian, A. Khorshidi, M. Mamaghani, A. Dadashi, M. Khoshnood Jalali, One-pot synthesis of tetrahydrobenzo[a]xanthen-11-one derivatives catalyzed by ruthenium chloride hydrate as a homogeneous catalyst, Can. J. Chem. 89 (2011) 623-627.

    31. [31] A. Khorshidi, Indole cyanation via C-H bond activation under catalysis of Ru(Ⅲ)- exchanged NaY zeolite (RuY) as a recyclable catalyst, Chin. Chem. Lett. 23 (2012) 903-906.[31] A. Khorshidi, Indole cyanation via C-H bond activation under catalysis of Ru(Ⅲ)- exchanged NaY zeolite (RuY) as a recyclable catalyst, Chin. Chem. Lett. 23 (2012) 903-906.

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  0
  • HTML全文浏览量:  0
文章相关
  • 收稿日期:  2013-08-15
  • 网络出版日期:  2013-10-08
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章