Citation: Zhi-Wei Chen, Na Zhang, Zhi-Hua Wang, Wei-Ke Su. An efficient synthesis of novel chromeno[3’, 4’:5, 6]pyrano[2, 3-b]indole derivatives[J]. Chinese Chemical Letters, ;2013, 24(3): 199-201. shu

An efficient synthesis of novel chromeno[3’, 4’:5, 6]pyrano[2, 3-b]indole derivatives

  • Corresponding author: Wei-Ke Su, 
  • Received Date: 6 November 2012
    Available Online: 4 January 2013

  • An efficient two-step method was described for the synthesis of chromeno[3',4':5,6]pyrano[2,3-b]indole derivatives. The three-component reaction of 4-hydroxycoumarin, variously substituted benzaldehydes and indolin-2-one was promoted by P2O5 in refluxing ethanol to give trimolecular adducts, which were then cyclized in 1,2-dichloroethane under reflux using POCl3.
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    1. [1]

      [1] C. Kalinski, H. Lemoine, J. Schmidt, et al., Multicomponent reactions as a powerful tool for generic drug synthesis, Synthesis 24 (2008) 4007-4011.

    2. [2]

      [2] Z.Q. Xu, K. Pupek, W.J. Suling, et al., Pyranocoumarin, a novel anti-TB pharmacophore: synthesis and biological evaluation against Mycobacterium tuberculosis, Bioorg. Med. Chem. 14 (2006) 4610-4626.

    3. [3]

      [3] W.F. Fong, X.L. Shen, C. Globisch, et al., Methoxylation of 3',4'-aromatic side chains improves P-glycoprotein inhibitory and multidrug resistance reversal activities of 7,8-pyranocoumarin against cancer cells, Bioorg. Med. Chem. 16 (2008) 3694-3703.

    4. [4]

      [4] C.R. Su, S.F. Yeh, C.M. Liu, et al., Anti-HBV and cytotoxic activities of pyranocoumarin derivatives, Bioorg. Med. Chem. 17 (2009) 6137-6143.

    5. [5]

      [5] B. Kongkathip, N. Kongkathip, A. Sunthitikawinsakul, et al., Anti-HIV-1 constituents from Clausena excavate: Part Ⅱ. Carbazoles and a pyranocoumarin, Phytother. Res. 19 (2005) 728-731.

    6. [6]

      [6] J.M. Khurana, B. Nand, P. Saluja, DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b] pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium, Tetrahedron 66 (2010) 5637-5641.

    7. [7]

      [7] J. Zheng, Y.Q. Li, Basic ionic liquid-catalyzed multicomponent synthesis of tetrahydrobenzo[b]pyrans and pyrano[c]chromenes, Mendeleev Commun. 21 (2011) 280-281.

    8. [8]

      [8] Z.W. Chen, Q. Zhu, W.K. Su, A novel sulfonic acid functionalized ionic liquid catalyzed multicomponent synthesis of 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione derivatives in water, Tetrahedron Lett. 52 (2011) 2601-2604.

    9. [9]

      [9] W.W. Ma, X. Wang, F.L. Yan, et al., Reusable melamine trisulfonic acid-catalyzed three-component synthesis of 7-alkyl-6H,7H-naphtho[1',2':5,6]pyrano[3,2-c] chromen-6-ones, Monatsh. Chem. 142 (2011) 163-167.

    10. [10]

      [10] Z.W. Chen, W.K. Su, J.H. Bi, Preparation of 7,12-dihydro-6H-chromeno[4,3-b] quinoline coumarin-like derivatives as antitumor agents, CN102584841A (18 July 2012).

    11. [11]

      [11] Z.W. Chen, J.H. Bi, W.K. Su, A novel method for one-pot synthesis of furo[3,2-c] coumarin derivatives form 4-hydroxycoumarin and arylglyoxal under microwave irradiation, Chin. J. Chem. 30 (2012) 1845-1850.

    12. [12]

      [12] Y. Jacquot, B. Refouvelet, L. Bermont, et al., Synthesis and cytotoxic activity of new 2,4-diaryl-4H,5H-pyrano[3,2-c]benzopyran-5-ones on MCF-7 cells, Pharmazie 57 (2002) 233-237.

    13. [13]

      [13] K.C. Nicolaou, J.L. Hao, M.V. Reddy, et al., Chemistry and biology of diazonamide A: second total synthesis and biological investigations, J. Am. Chem. Soc. 126 (2004) 12897-12906.

    14. [14]

      [14] I.M. EL-Deen, F.F. Mahmoud, Synthesis and chemical behavior of 2-chloro-3-(20-thienoylmethyl)quinoxaline towards some nucleophilic reagents, Phosphorus, Sulfur, Silicon Relat. Elem. 165 (2000) 205-212.

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