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Australian Journal of Chemistry Australian Journal of Chemistry Society
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RESEARCH ARTICLE

An Organobase (TBD)-Anchored Mesoporous Silica Nanoparticle-Catalyzed Green Synthesis of Dihydropyrano[2,3-c]pyrazoles

Bikash Karmakar
+ Author Affiliations
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Gobardanga Hindu College, Department of Chemistry, Khantura, North 24 Parganas-743273, India. Email: bikashkarm@gmail.com

Australian Journal of Chemistry 69(10) 1117-1123 https://doi.org/10.1071/CH15812
Submitted: 24 December 2015  Accepted: 20 March 2016   Published: 26 April 2016

Abstract

An efficient, mild, and environmental friendly method has been developed for the synthesis of dihydropyrano[2,3-c]pyrazole in ethanolic water over 1,5,7-triazabicyclo-[4,4,0]-dec-1-ene (TBD)-anchored mesoporous silica nanoparticle catalyst. The method involves the assembly of ethyl acetoacetate, hydrazine hydrate, different aldehydes, and malononitrile. It affords the corresponding product in high yield with short reaction times, while employing a very low loading of catalyst. The catalyst was reused several times without significant loss in activity.


References

[1]  (a) A. Gomtsyan, Chem. Heterocycl. Compd. 2012, 48, 7.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XntFOntbs%3D&md5=f863d065a3a5935489e03e127e8a0150CAS |
      (b) Y. W. Chin, M. J. Balunas, H. B. Chai, A. D. Kinghorn, AAPS J. 2006, 8, E239.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) F. E. Koehn, G. T. Carter, Nat. Rev. Drug Discovery 2005, 4, 206.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) E. H. Hughes, J. V. Shanks, Metab. Eng. 2002, 4, 41.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  (a) S. L. Schreiber, Science 2000, 287, 1964.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXhvFyrurw%3D&md5=50b7938ffb9cefe72f1270535a7438a4CAS | 10720315PubMed |
         (b) N. K. Terett, Combinatorial Chemistry 1998 (Oxford University Press: New York, NY).

[3]  A. Dömling, I. Ugi, Angew. Chem., Int. Ed. Engl. 2000, 39, 3168.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) W. Leitner, Green Chem. 2007, 9, 923.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) I. T. Horváth, Green Chem. 2008, 10, 1024.
         | Crossref | GoogleScholarGoogle Scholar |
         (c) C. J. Li, T. H. Chan, Organic Reaction in Aqueous Media 1997 (Wiley: New York, NY).

[5]  E. S. El‐Tamany, F. A. El‐Shahed, B. H. Mohamed, J. Serb. Chem. Soc. 1999, 64, 9.
         | 1:CAS:528:DyaK1MXhvVOqsro%3D&md5=ed0651ee480f4d0ea0b13114e0b2131aCAS |

[6]  Z. H. Ismail, G. M. Aly, M. S. El‐Degwi, H. I. Heiba, M. M. Ghorab, Egypt. J. Biotechnol. 2003, 13, 73.
         | 1:CAS:528:DC%2BD3sXmsFGit78%3D&md5=d492e121fe0bd8dc11a5c451d745852aCAS |

[7]  M. E. A. Zaki, H. A. Soliman, O. A. Hiekal, A. E. Z. Rashad, Z. Naturforsch C: J. Biosci. 2006, 61, 1.
         | 1:CAS:528:DC%2BD28XjsFCgur0%3D&md5=6daa9359e89ce2d452eaff6ecf894347CAS |

[8]  J. L. Wang, D. Liu, Z. J. Zheng, S. Shan, X. Han, S. M. Srinivasula, C. M. Croce, E. S. Alnemri, Z. Huang, Proc. Natl. Acad. Sci. USA 2000, 97, 7124.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXksVKit78%3D&md5=af5155e2e21d32bf7992448e1d40acd2CAS | 10860979PubMed |

[9]  (a) F. M. Abdelrazek, P. Metz, N. H. Metwally, S. F. El‐Mahrouky, Arch. Pharm. 2006, 339, 456.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XovVWgs70%3D&md5=756711a9b67ec2df458f5c14b4dcc30bCAS |
      (b) F. M. Abdelrazek, P. Metz, O. Kataeva, A. Jaeger, S. F. El‐Mahrouky, Arch. Pharm. 2007, 340, 543.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  N. Foloppe, L. M. Fisher, R. Howes, A. Potter, A. G. S. Robertson, A. E. Surgenor, Bioorg. Med. Chem. 2006, 14, 4792.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XltFOmtb8%3D&md5=2b03ea1cedfaef42293dcdad967c909aCAS | 16574416PubMed |

[11]  (a) H. Junek, H. Aigner, Chem. Ber. 1973, 106, 914.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3sXhtlKhsrg%3D&md5=eeed4e0f5025614f15aa842a3a540554CAS |
      (b) H. Wamhoff, E. Kroth, K. Strauch, Synthesis 1993, 1993, 1129.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) G. Tacconi, G. Gatti, G. Dasimoni, J. Prakt. Chem. 1980, 322, 831.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  H. H. Otto, Arch. Pharm 1974, 307, 444.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2cXkslOrsbw%3D&md5=591c8fd0276863fac6e12b9052aaa7c1CAS |

[13]  G. V. Klokol, S. G. Krivokolysko, V. D. Dyachenko, V. P. Litvinov, Chem. Heterocycl. Compd. 1999, 35, 1183.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXislyntbY%3D&md5=bd09cd7df2bd4eda38671e496d5c5c27CAS |

[14]  (a) M. Babaie, H. Sheibani, Arabian J. Chem. 2011, 4, 159.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjs1ylu7k%3D&md5=2a8934cd60680ffda68f57766f0b9605CAS |
      (b) A. Siddekha, A. Nizam, M. A. Pasha, Spectrochim. Acta, Part A 2011, 81, 431.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) S. Hamood, S. Azzam, M. A. Pasha, Tetrahedron Lett. 2012, 50, 6834.
      (d) X. S. Wang, D. Q. Shi, L. C. Rong, C. S. Yao, G. Y. Dai, Jiegou Huaxue 2003, 22, 331.
      (e) A. Siddekha, A. Nizam, M. A. Pasha, Spectrochim. Acta, Part A 2011, 81, 431.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) S. A. El-Assaly, Pharma Chem 2011, 3, 81.
      (g) A. Sharanin Yu, L. G. Sharanina, V. V. Puzanova, Zh. Org. Khim. 1983, 19, 2609.
      (h) Y. A. Sharanin, L. G. Sharanina, V. V. Puzanova, J. Org. Chem. USSR (Engl. Transl.) 1983, 221.
      (i) Y. Peng, G. Song, R. Dou, Green Chem. 2006, 8, 573.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) G. Vasuki, K. Kumaravel, Tetrahedron Lett. 2008, 49, 5636.
         | Crossref | GoogleScholarGoogle Scholar |
      (k) S. W. Kshirsagar, N. R. Patil, S. D. Samant, Synth. Commun. 2011, 41, 1320.
         | Crossref | GoogleScholarGoogle Scholar |
      (l) Y. Peng, G. Song, F. Huang, Monatsh. Chem. 2005, 136, 727.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  (a) T.-S. Jin, R.-Q. Zhao, T.-S. Li, ARKIVOC 2006, 2006(xi), 176.
      (b) T.-S. Jin, A.-Q. Wang, Z.-L. Cheng, J.-S. Zhang, T.-S. Li, Synth. Commun. 2005, 35, 137.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) G. Vasuki, K. Kandhasamy, Tetrahedron Lett. 2008, 49, 5636.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) S. Gogoi, C.-G. Zhao, Tetrahedron Lett. 2009, 50, 2252.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) K. Kanagaraj, K. Pitchumani, Tetrahedron Lett. 2010, 51, 3312.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) J. Ebrahimi, A. Mohanndi, V. Pakjoo, E. Bahramzadeh, A. Habibi, J. Chem. Sci. 2012, 124, 1013.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) H. Mecadon, M. R. Rohman, I. Kharbangar, B. M. Laloo, I. Kharkongor, M. Rajbangshi, B. Myrboh, Tetrahedron Lett. 2011, 52, 3228.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) H. V. Chavan, S. B. Babar, R. U. Hoval, B. P. Bandgar, Bull. Korean Chem. Soc. 2011, 32, 3963.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) M. B. M. Reddy, V. P. Jayashankara, M. A. Pasha, Synth. Commun. 2010, 40, 2930.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) H. G. Kathrotiya, R. G. Patel, M. P. Patel, J. Serb. Chem. Soc. 2012, 77, 983.
         | Crossref | GoogleScholarGoogle Scholar |
      (k) A. S. Nagarajan, B. S. R. Reddy, Synlett 2009, 2002.

[16]  (a) B. Karmakar, A. Nayak, B. Chowdhury, J. Banerji, ARKIVOC 2009, 2009(xii), 209.
      (b) G. Postole, B. Chowdhury, B. Karmakar, K. Pinki, J. Banerji, A. Auroux, J. Catal. 2010, 269, 110.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) B. Karmakar, B. Chowdhury, J. Banerji, Catal. Commun. 2010, 11, 601.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) B. Karmakar, J. Banerji, Tetrahedron Lett. 2010, 51, 3855.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) B. Karmakar, A. Sinhamahapatra, A. B. Panda, J. Banerji, B. Chowdhury, Appl. Catal., A 2011, 392, 111.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) B. Karmakar, J. Banerji, Tetrahedron Lett. 2011, 52, 4957.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) B. Karmakar, J. Banerji, Tetrahedron Lett. 2011, 52, 6584.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  (a) T. Yokoi, Y. Kubota, T. Tatsumi, Appl. Catal., A. 2012, 421–422, 14.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) W. Xie, M. Fan, Bioresour. Technol. 2013, 139, 388.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) K. Sarkar, M. Nandi, M. Islam, M. Mubarak, A. Bhaumik, Appl. Catal., A 2009, 352, 81.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) A. Corma, A. Fuerte, M. Iglesias, F. Sanchez, J. Mol. Catal. Chem. 1996, 107, 225.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) A. Sakthivel, J. Zhao, G. Raudaschl-Sieber, M. Hanzlik, A. S. T. Chiang, F. E. Kühn, Appl. Catal., A 2005, 281, 267.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) K. Ariga, A. Vinu, J. P. Hill, T. Mori, Coord. Chem. Rev. 2007, 251, 2562.
         | Crossref | GoogleScholarGoogle Scholar |

[18]  B. Yu, J.-N. Xie, C.-L. Zhong, W. Li, L.-N. He, ACS Catal. 2015, 5, 3940.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXovVSns7Y%3D&md5=b1b7581d83f258aaf12e51e997f87956CAS |