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RESEARCH ARTICLE
Contents Vol 69(9)

A Green Approach for the Synthesis of Novel 7,11-Dihydro-6H-chromeno[3,4-e]isoxazolo[5,4-b]pyridin-6-one Derivatives Using Acidic Ionic Liquid [C4mim][HSO4]

Sudesh Kumari A , M. Rajeswari A and Jitender M. Khurana A B
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, University of Delhi, Delhi 110007, India.

B Corresponding author. Email: jmkhurana@chemistry.du.ac.in

Australian Journal of Chemistry 69(9) 1049-1053 https://doi.org/10.1071/CH16014
Submitted: 12 January 2016  Accepted: 16 March 2016   Published: 18 April 2016

Abstract

A multicomponent reaction capable of affording a wide range of novel 7,11-dihydro-6H-chromeno[3,4-e]isoxazolo[5,4-b]pyridin-6-one derivatives via one-pot three-component condensation of 4-hydroxycoumarin, aromatic aldehydes, and 5-amino-3-methylisoxazole in ionic liquid 1-butyl-3-methylimidazolium hydrogen sulfate ([C4mim][HSO4]) is reported. Structures have been confirmed by spectral and X-ray studies. Crystal packing of 4b has also been reported. Green solvent, short reaction time, easy workup, and high yields are the salient features of the present protocol.


References

[1]  F. Borges, F. Roleira, N. Milhazes, L. Santana, E. Uriarte, Curr. Med. Chem. 2005, 12, 887.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXjtVCjsb4%3D&md5=0386103adbda6aba75b08aeab4332013CAS | 15853704PubMed |

[2]  A. Parvez, J. Meshram, V. Tiwari, J. Sheik, R. Dongre, M. H. Youssoufi, T. B. Hadda, Eur. J. Med. Chem. 2010, 45, 4370.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXpvFKhtbk%3D&md5=3f362ca335d05b985d10793b49e89c78CAS | 20591539PubMed |

[3]  A. Sanchez-Recillas, G. N. Vazquez, S. H. Figueroa, M. Y. Rios, M. I. Barajas, S. E. Soto, Eur. J. Med. Chem. 2014, 77, 400.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXmtVSjsL8%3D&md5=8a0ef595e2517dcf6a7034f824a8f322CAS | 24681028PubMed |

[4]  M. Camur, M. Duemus, M. Bulut, Polyhedron 2012, 41, 92.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XnsVGltL0%3D&md5=812c82861a2d8a6ff33b38408f0c597fCAS |

[5]  (a) H. Turki, S. Abid, S. F. Forgues, R. E. Gharbi, Dyes Pigm. 2007, 73, 311.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtFent7nF&md5=dd5d3e6f415cbd2a8a4dc3ab448d0438CAS |
      (b) H. M. Kim, X. Z. Fang, P. R. Yang, J. S. Yi, Y. G. Ko, M. J. Piao, Tetrahedron Lett. 2007, 48, 2791.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  R. M. Melavanki, R. A. Kusanur, M. V. Kulakarni, J. S. Kadadevarmath, J. Lumin. 2008, 128, 573.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXltVGqtg%3D%3D&md5=92f43d2dca45a30e0142ba4822745e25CAS |

[7]  T. K. Kim, D. N. Lee, H. J. Kim, Tetrahedron Lett. 2008, 49, 4879.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXotFegsLw%3D&md5=ae979cdf6470ed34a307a8c8c9126281CAS |

[8]  (a) J. Cullen, M. Hinkhouse, M. Grady, A. Gaut, J. Liu, Y. Zhang, C. Weydert, F. Domann, L. Oberley, Cancer Res. 2003, 63, 5513.
         | 1:CAS:528:DC%2BD3sXntlersr8%3D&md5=fd316e46daa786e162c9679c5282e695CAS | 14500388PubMed |
      (b) A. Mironov, A. Colanzi, R. Polishchuk, G. Beznoussenko, A. Mironov, A. Fusella, G. Di Tullio, M. Silletta, D. Corda, M. De Matteis, A. Luini, Eur. J. Cell Biol. 2004, 83, 263.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  (a) P. Conti, C. Dallanoce, M. D. Amici, C. D. Micheli, K. N. Klotz, Bioorg. Med. Chem. 1998, 6, 401.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXislCmtrc%3D&md5=2d0e5fe0e4d5d381316fb4983d569e77CAS | 9597184PubMed |
      (b) M. G. Gordaliza, T. Faircloth, M. A. Castro, J. M. M. Corral, M. L. Lopez-Vazquez, A. San Feliciano, J. Med. Chem. 1996, 39, 2865.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) T. Kwon, A. S. Heimann, E. T. Oriaku, K. Yoon, J. Med. Chem. 1995, 38, 1048.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) Y. Y. Kang, K. J. Shin, K. H. Yo, K. J. Seo, C. Y. Hong, C. S. Lee, S. Y. Park, D. J. Kim, S. W. Park, Bioorg. Med. Chem. Lett. 2000, 10, 95.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  T. M. V. D. Pinho e Melo, Curr. Org. Chem. 2005, 9, 925.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXls1Grsbk%3D&md5=30f7f4f467a7ba7ea4b7080091673defCAS |

[11]  V. A. Osyanin, D. V. Osipov, Y. N. Klimochkin, Tetrahedron 2012, 68, 5612.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XntlSqsrc%3D&md5=de7e241378e9f0736e6c4c6e9898f6adCAS |

[12]  N. M. Evdokimov, A. S. Kireev, A. A. Yakovlenko, M. Y. Antipin, I. V. Magedov, A. Kornienko, J. Org. Chem. 2007, 72, 3443.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXjvFKgsL8%3D&md5=dda278c2d6da1d6c16f0281adb1a5b35CAS | 17408286PubMed |

[13]  D. R. Anderson, S. Hegde, E. Reinhard, L. Gomez, W. F. Vernier, L. Lee, S. Liu, A. Sambandam, P. A. Snider, L. Masih, Bioorg. Med. Chem. Lett. 2005, 15, 1587.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhvF2ntbw%3D&md5=95bbbb4f17e6908710b12b2b79699ed4CAS | 15745802PubMed |

[14]  J. A. Bristol, E. H. Gold, I. Gross, R. G. Lovey, J. F. Long, J. Med. Chem. 1981, 24, 1010.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3MXksFCkurw%3D&md5=2fc2dd1a1bd2c95e7b5f74369a451eecCAS | 7328593PubMed |

[15]     (a) L. F. Tietze, G. Brasche, K. M. Gericke, Domino Reactions in Organic Synthesis 2006 (Wiley-VCH: Weinheim).
      (b) A. S. Ivanov, Chem. Soc. Rev. 2008, 37, 789.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. de Meijere, P. von Zezschwitz, S. Brase, Acc. Chem. Res. 2005, 38, 413.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  (a) L. F. Tietze, Chem. Rev. 1996, 96, 115.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XjsVOhsQ%3D%3D&md5=074d0dc3f2c37f621ecffadc2e6abf5cCAS | 11848746PubMed |
      (b) D. Enders, M. R. M. Huttl, C. Grondal, G. Raabe, Nature 2006, 441, 861.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  P. Tundo, P. Anastas, D. S. Black, Pure Appl. Chem. 2000, 72, 1207.
         | 1:CAS:528:DC%2BD3cXotFKqsrY%3D&md5=95deffbe2dc153f453b18a591c9d7790CAS |

[18]  (a) M. J. Earle, J. M. S. S. Esperanc, M. A. Gilea, J. N. C. Lopes, L. P. N. Rebelo, J. W. Magee, K. R. Seddon, J. A. Widegren, Nature 2006, 439, 831.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhsVSkurk%3D&md5=57e46a5b5740fbd7b72ee1c7081a1503CAS | 16482154PubMed |
      (b) K. Ghandi, Green Sustainable Chem. 2014, 4, 44.
         | Crossref | GoogleScholarGoogle Scholar |

[19]  K. R. Seddon, Kinet. Catal. 1996, 37, 693.
         | 1:CAS:528:DyaK28XmsV2js7Y%3D&md5=619006a884476b81e1376e86261586a5CAS |

[20]  (a) A. Domling, Chem. Rev. 2006, 106, 17.
         | Crossref | GoogleScholarGoogle Scholar | 16402771PubMed |
      (b) C. Hulme, V. Gore, Curr. Med. Chem. 2003, 10, 51.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  (a) G. Khanna, A. Chaudhary, J. M. Khurana, Tetrahedron Lett. 2014, 55, 6652.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhslOrtb7I&md5=4efbebb0a5f5f14dc8566e5d19620e14CAS |
      (b) J. Sindhu, H. Singh, J. M. Khurana, Mol. Diversity 2014, 18, 345.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) H. Singh, J. Sindhu, J. M. Khurana, C. Sharma, K. R. Aneja, RSC Adv. 2014, 4, 5915.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) H. Singh, J. Sindhu, J. M. Khurana, RSC Adv. 2013, 3, 22360.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) P. Saluja, A. Chaudhary, J. M. Khurana, Tetrahedron Lett. 2014, 55, 3431.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) J. M. Khurana, A. Chaudhary, A. Lumb, B. Nand, Green Chem. 2012, 14, 2321.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) J. M. Khurana, A. Chaudhary, B. Nand, A. Lumb, Tetrahedron Lett. 2012, 53, 3018.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) H. Singh, J. Sindhu, J. M. Khurana, C. Sharma, K. R. Aneja, Eur. J. Med. Chem. 2014, 77, 145.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) M. Rajeswari, J. Sindhu, H. Singh, J. M. Khurana, RSC Adv. 2015, 5, 39686.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) H. Singh, S. Kumari, J. M. Khurana, Chin. Chem. Lett. 2014, 25, 1336.
         | Crossref | GoogleScholarGoogle Scholar |
      (k) J. Sindhu, H. Singh, J.M. Khurana, C. Sharma, K.R. Aneja, Chin. Chem. Lett. 2015, 26, 50.
         | Crossref | GoogleScholarGoogle Scholar |

[22]  K. V. Sashidhara, G. R. Palnati, L. R. Singh, A. Upadhyay, S. R. Avula, A. Kumar, R. Kant, Green Chem. 2015, 17, 3766.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXptFOqs7s%3D&md5=535371ec1e4449323fa0e49c7c2e1a46CAS |

[23]  G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Adv. 2008, 64, 112.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVGhurzO&md5=1965db3178cb384357dbea613ab9f64bCAS |

[24]  L. J. Farrugia, WinGX Version 1.80.05: An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-Ray Diffraction Data 1997 (Department of Chemistry, University of Glasgow: Glasgow).