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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Solvent-free Synthesis of Novel Benzothiazole-substituted 4-Thiazolidinones Using Nano Silica-bonded 5-n-Propyl-octahydro-pyrimido[1,2-a]azepinium Chloride as Catalyst

Robabeh Baharfar A B and Narges Shariati A
+ Author Affiliations
- Author Affiliations

A Faculty of Chemistry, University of Mazandaran, PO Box 47415, Babolsar, Iran.

B Corresponding author. Email: baharfar@umz.ac.ir

Australian Journal of Chemistry 67(11) 1646-1655 https://doi.org/10.1071/CH13712
Submitted: 2 January 2014  Accepted: 2 March 2014   Published: 10 April 2014

Abstract

A series of novel benzothiazole-substituted 4-thiazolidinones were synthesised by the one-pot reaction of rhodanine-3-acetic acid derivatives, 2-aminothiophenol, and triphenyl phosphite in the presence of nano silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (NSB-DBU) as heterogeneous reusable nanocatalyst under solvent-free conditions in high yields.


References

[1]  K. Wang, F. P. Guenqerich, Chem. Res. Toxicol. 2012, 25, 1740.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XptFCisrc%3D&md5=647f817d79805ce9ee58a7908a42287aCAS | 22734839PubMed |

[2]  (a) W. Huang, G. F. Yang, Bioorg. Med. Chem. 2006, 14, 8280.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtFOjt7zL&md5=cc0ca5f4fea11bb9a0aec71cd7f73af3CAS | 17008103PubMed |
      (b) C. Sheng, X. Che, W. Wang, S. Wang, Y. Cao, J. Yao, Z. Miao, W. Zhang, Eur. J. Med. Chem. 2011, 46, 1706.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  (a) P. Patel, J. Pillai, N. Darji, B. Patel, Int. J. Drug Res. Technol. 2012, 2, 170.
         | 1:CAS:528:DC%2BC38Xhtl2jt7vL&md5=498ee2b7125e1ceeaab9e5f9ec1fc17fCAS |
      (b) S. Shafi, M. M. Alam, N. Mulakayala, C. Mulakayala, G. Vanaja, A. M. Kalle, R. Pallu, M. S. Alam, Eur. J. Med. Chem. 2012, 49, 324.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) S. Bondock, W. Fadaly, M. A. Metwally, Eur. J. Med. Chem. 2009, 44, 4813.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsVCksLzF&md5=c2d3a535653580e1ae1a77c2669cd09fCAS | 19683840PubMed |
      (b) S. Saeed, N. Rashid, P. G. Jones, M. Ali, R. Hussain, Eur. J. Med. Chem. 2010, 45, 1323.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  S. R. Nagarajan, G. A. De Crescenzo, D. P. Getman, H. F. Lu, J. A. Sikorski, J. L. Walker, J. J. McDonald, K. A. Houseman, G. P. Kocan, N. Kishore, P. P. Mehta, C. L. Funkes-Shippy, L. Blystone, Bioorg. Med. Chem. 2003, 11, 4769.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXnvVymu70%3D&md5=c33722cc440e386cc92e66574364b4aaCAS | 14556792PubMed |

[6]  (a) S. L. Johnson, L. H. Chen, E. Barile, A. Emdadi, M. Sabet, H. Yuan, J. Wei, D. Guiney, M. Pellecchia, Bioorg. Med. Chem. 2009, 17, 3352.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXltFSqtbw%3D&md5=519bf321aa7be5ec4b590166a5fca49dCAS | 19359184PubMed |
      (b) K. M. Khan, F. Rahim, S. A. Halim, M. Taha, M. Khan, S. Perveen, M. Zaheer-ul Haq, M. A. Mesaik, M. I. Choudhary, Bioorg. Med. Chem. 2011, 19, 4286.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) L. Huang, T. Su, W. Shan, Z. Luo, Y. Sun, F. He, X. Li, Bioorg. Med. Chem. 2012, 20, 3038.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  K. Babaoglu, M. A. Page, V. C. Jones, M. R. McNeil, C. Dong, J. H. Naismith, R. E. Lee, Bioorg. Med. Chem. Lett. 2003, 13, 3227.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXmvV2ltrg%3D&md5=8c1aba62a2509545dc61fbe1d1f123a8CAS | 12951098PubMed |

[8]  (a) V. Gududuru, E. Hurh, J. T. Dalton, D. D. Miller, Bioorg. Med. Chem. Lett. 2004, 14, 5289.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXnvFWqsb4%3D&md5=3d3c473a372b29f9bd4fcffe5d4c7e28CAS | 15454213PubMed |
      (b) R. OttanĂ , S. Carotti, R. Maccari, I. Landini, G. Chiricosta, B. Caciagli, M. G. Vigorita, E. Mini, Bioorg. Med. Chem. Lett. 2005, 15, 3930.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  (a) C. Dwivedi, T. K. Gupta, S. S. Parmar, J. Med. Chem. 1972, 15, 553.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE38XksVejtbs%3D&md5=056a5e7525b5bd0a84d62f77eec713e9CAS | 5035284PubMed |
      (b) S. S. Parmar, C. Dwivedi, A. Chaudhari, T. K. Gupta, J. Med. Chem. 1972, 15, 99.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  K. Omar, A. Geronikaki, P. Zoumpoulakis, C. Camoutsis, M. Sokovic, A. Ciric, J. Glamoclija, Bioorg. Med. Chem. 2010, 18, 426.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsFykurnO&md5=46b5e82b3bb718a506d3121e900d3949CAS | 19914077PubMed |

[11]  (a) S. K. Chaudhari, M. Verma, A. K. Chaturvedi, S. S. Parmar, J. Pharm. Sci. 1975, 64, 614.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2MXktVShtbs%3D&md5=c857aee1b428ebde390303e7bbb6d214CAS | 167147PubMed |
      (b) M. Chaudhary, S. S. Parmar, S. K. Chaudhary, A. K. Chaturvedi, B. V. R. Sastry, J. Pharm. Sci. 1976, 65, 443.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  D. Havrylyuk, L. Mosula, B. Zimenkovsky, O. Vasylenko, A. Gzella, R. Lesyk, Eur. J. Med. Chem. 2010, 45, 5012.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht1KrtrjM&md5=2fdeeb0d10051c367afedd811b7d449aCAS | 20810193PubMed |

[13]  R. S. Varma, Green Chem. 1999, 1, 43.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXit1ylsbo%3D&md5=b45cc93390a1190e67b1d2f02d9163d5CAS |

[14]  (a) S. Safaei, I. Mohammadpoor-Baltork, A. R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, Catal. Sci. Technol. 2013, 3, 2717.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsVSltrzP&md5=934890f42339b81086fc6e0ba776d2daCAS |
      (b) B. Samani Ghaleh Taki, V. Mirkhani, I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, M. Rostami, A. R. Khosropour, J. Inorg. Organomet. Polym. 2013, 23, 758.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  (a) R. Reed, R. Reau, F. Dahan, G. Bertrand, Angew. Chem. Int. Ed. Engl. 1993, 32, 399.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) N. Ghosh, Synlett 2004, 2004, 574.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) M. Baidya, H. Mayr, Chem. Commun. 2008, 1792.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) A. G. Ying, L. Liu, G. Wu, F. G. Chen, X. Z. Chen, W. D. Ye, Tetrahedron Lett. 2009, 50, 1653.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  (a) G. L. Zhao, Y. L. Shi, M. Shi, Org. Lett. 2005, 7, 4527.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXps1equrg%3D&md5=50e4e57e0610a1c6e9d65810d0e25255CAS | 16178575PubMed |
      (b) L. Z. Dai, Y. L. Shi, G. L. Zhao, M. Shi, Chem. Eur. J. 2007, 13, 3701.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) K. E. Price, C. L. Aboussafy, B. M. Lillie, R. W. McLaughlin, J. Mustakis, K. W. Het-tenbach, J. M. Hawkins, R. Vaidyanathan, Org. Lett. 2009, 11, 2003.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) K. N. Kumar, K. Sreeramamurthy, S. Palle, K. Mukkanti, P. Das, Tetrahedron Lett. 2010, 51, 899.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) C. LarrivĂ©e-Aboussafy, B. P. Jones, K. E. Price, M. A. Hardink, R. W. McLaughlin, B. M. Lillie, J. M. Hawkins, R. Vaidyanathan, Org. Lett. 2010, 12, 324.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  (a) X. Zhang, W. Cui, W. Han, Y. Zhang, S. Liu, W. Mu, Y. Chang, R. Hu, React. Kinet. Catal. Lett. 2009, 98, 349.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsVahu7zJ&md5=20e64b448baf6a68f867524a1b17b730CAS |
      (b) X. Zhang, Y. Zhang, Y. Yang, Q. Wei, X. Zhang, React. Kinet. Catal. Lett. 2008, 94, 385.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. Hasaninejad, N. Golzar, M. Beyrati, A. Zare, M. M. Doroodmand, J. Mol. Catal. A-Chem. 2013, 372, 137.
         | Crossref | GoogleScholarGoogle Scholar |

[18]  (a) R. Baharfar, N. Shariati, C. R. Chim. 2013, in press.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) R. Baharfar, S. M. Baghbanian, S. M. Vahdat, Tetrahedron Lett. 2011, 52, 6018.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) R. Baharfar, N. Porahmad, Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 1988.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) R. Baharfar, S. M. Vahdat, F. G. Hakimabadi, Monatsh. Chem. 2009, 140, 489.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) R. Baharfar, R. Azimi, Chinese Chem. Lett. 2011, 22, 943.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) R. Baharfar, R. Azimi, Syn. Com. 2014, 44, 89.
         | Crossref | GoogleScholarGoogle Scholar |

[19]  J. H. Li, X. Ch. Hu, Y. X. Xie, Tetrahedron Lett. 2006, 47, 9239.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht1KktbvO&md5=55b71ea0a979f4a13af4eea1ac8dfa61CAS |