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Synthesis of 2-amide-3-carboxylate-4-aryl-4H-chromene derivatives

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Abstract

Tetrabutyl ammonium bromide (TBAB) catalyzed one-pot synthesis of 4H-chromene via a three-component cyclocondensation of aryl aldehydes, cyanoacetate and dimedone in green media–water. Then, 4H-chromene reacted with acyl chloride in acetonitrile at refluxing with catalytic amount of DMAP to yield the title compounds in good yields. The structures of all title compounds were confirmed by 1H NMR, MS and elementary analyses. The X-ray crystallography of compound 3n indicated that there were strong intermolecular hydrogen bonds.

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References

  1. K. Singh, J. Singh, H. Singh, Tetrahedron 52, 14273–14280 (1996)

    Article  CAS  Google Scholar 

  2. S. Hatokeyama, N. Ochi, H. Numata et al., J. Chem. Soc. Chem. Commun. 17, 1202–1204 (1988)

    Article  Google Scholar 

  3. G.T. Brooks, A.P. Ottridge, R.C. Jennings et al., Pestic. Sci. 16, 571–588 (1985)

    Article  CAS  Google Scholar 

  4. E.C. Witte, P. Neubert, A. Roesch, Ger. Offen. DE3427985, (1986)

  5. N. Chand, W. Diamantis, R.D. Sofia, Brit. J. Pharmcol. 87, 443–448 (1986)

    Article  CAS  Google Scholar 

  6. T. Hyana, H. Saimoto, Jpn Kokai Tokkyo Koho. JP 62181276, (1987)

  7. V.B. Chavan, G.S. Sarate, N.S. Tankhiwale et al., Indian J. Anaesth. 42, 192–194 (1994)

    Google Scholar 

  8. Z.J. Liu, Z.R. Li, Chin. J. Org. Chem. 11, 433–436 (1991)

    CAS  Google Scholar 

  9. V.F. Paula, L.C.A. Barbosa, A.J. Demuner et al., Pest Manage. Sci. 56, 168–174 (2000)

    Article  Google Scholar 

  10. J.S. Pizey, R.L. Wain, J. Sci. Food. Agric. 10, 577–584 (1959)

    Article  CAS  Google Scholar 

  11. M. Suarez, E. Salfran, Y. Verdecia et al., Tetrahedron 58, 953–960 (2002)

    Article  CAS  Google Scholar 

  12. Q.Y. Zhuang, N. Wu, D.Q. Shi et al., Chin. J. Org. Chem. 26, 1217–1220 (2006)

    CAS  Google Scholar 

  13. S.J. Tu, Y. Gao, C. Guo et al., Synth. Commun. 32, 2137–2141 (2002)

    Article  CAS  Google Scholar 

  14. Z.Q. Jiang, S.J. Ji, J. Lu et al., Chin. J. Chem. 23, 1085–1089 (2005)

    Article  CAS  Google Scholar 

  15. I. Devi, P.J. Bhuyan, Tetrahedron Lett. 45, 8625–8627 (2004)

    Article  CAS  Google Scholar 

  16. L.C. Rong, X.Y. Li, H.Y. Wang et al., Synth. Commun. 36, 2363–2369 (2006)

    Article  CAS  Google Scholar 

  17. G. Kaupp, M.R. Naimi-Zamal, J. Schmeyers, Tetrahedron 59, 3753–3760 (2003)

    Article  CAS  Google Scholar 

  18. C.J. Li, Chem. Rev. 93, 2023–2035 (1993)

    Article  CAS  Google Scholar 

  19. A. Lubineau, Chem. Ind. (London) 4, 123–126 (1996)

    Google Scholar 

  20. A. Meijer, S. Otto, J.B. Engberts, J. Org. Chem. 63, 8989–8994 (1998)

    Article  CAS  Google Scholar 

  21. R. Ballini, G. Bosica, Tetrahedron Lett. 37, 8027–8030 (1996)

    Article  CAS  Google Scholar 

  22. R. Ballini, G. Bosica, J. Org. Chem. 62, 425–427 (1997)

    Article  CAS  Google Scholar 

  23. F. Bigi, S. Carloni, L. Ferrari et al., Tetrahedron Lett. 42, 5203–5205 (2001)

    Article  CAS  Google Scholar 

  24. G.M. Ziarani, A. Abbasi, A. Badiei et al., J. Chem. 8, 293–299 (2011)

    CAS  Google Scholar 

  25. S.B. Bandgar, B.P. Bandga, B.L. Korbad et al., Aust. J. Chem. 60, 305–307 (2007)

    Article  CAS  Google Scholar 

  26. X.S. Wang, D.Q. Shi, S.J. Tu et al., Synth. Commun. 33, 119–126 (2003)

    Article  CAS  Google Scholar 

  27. Q.Y. Wang, Master’s degree thesis of Hubei University, China, (2009)

  28. S.J. Tu, H. Wang, J.Q. Feng et al., Synth. Commun. 31, 2663–2666 (2001)

    Article  CAS  Google Scholar 

  29. S.J. Tu, C.B. Miao, Y. Gao et al., Chin. J. Chem. 20, 703–706 (2002)

    Article  CAS  Google Scholar 

  30. D.Q. Shi, S. Zhang, Q.Y. Zhuang, Chin. J. Org. Chem. 25, 1570–1574 (2005)

    CAS  Google Scholar 

  31. G.M. Sheldrick, SHELXS-97: program for crystal structure refinement; Göttingen, (1997)

  32. SAINT and SMART; Bruker AXS: Madison, (2003)

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Acknowledgments

We are grateful to financial support from the National NSFC (No.21162007), Project for Department of Education, Hainan Province (No.Hj2009-19) and Hainan University Postdoctoral Research Foundation.

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Authors and Affiliations

  1. Key Laboratory of Protection and Development Utilization of Tropical Crop Germplasm Resources, Ministry of Education, College of Environment and Plant Protection, Hainan University, Haikou, Hainan, 570228, People’s Republic of China

    Zhi-gang Zeng, Lan-ying Wang, Yang Cao & Yan-ping Luo

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  1. Zhi-gang Zeng
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  2. Lan-ying Wang
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  3. Yang Cao
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  4. Yan-ping Luo
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Correspondence to Yan-ping Luo.

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Zeng, Zg., Wang, Ly., Cao, Y. et al. Synthesis of 2-amide-3-carboxylate-4-aryl-4H-chromene derivatives. Res Chem Intermed 38, 1751–1760 (2012). https://doi.org/10.1007/s11164-012-0500-6

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