CSIRO Publishing blank image blank image blank image blank imageBooksblank image blank image blank image blank imageJournalsblank image blank image blank image blank imageAbout Usblank image blank image blank image blank imageShopping Cartblank image blank image blank image You are here: Journals > Australian Journal of Chemistry   
Australian Journal of Chemistry
Journal Banner
  An international journal for chemical science
 
blank image Search
 
blank image blank image
blank image
 
  Advanced Search
   

Journal Home
About the Journal
Editorial Structure
Contacts
For Advertisers
Content
Online Early
Current Issue
Just Accepted
All Issues
Virtual Issues
Special Issues
Research Fronts
Sample Issue
Covers
For Authors
General Information
Scope
Submit Article
Author Instructions
Open Access
For Referees
Referee Guidelines
Review an Article
For Subscribers
Subscription Prices
Customer Service
Print Publication Dates

blue arrow e-Alerts
blank image
Subscribe to our Email Alert or RSS feeds for the latest journal papers.

red arrow Connect with us
blank image
facebook twitter LinkedIn

Affiliated with RACI

Royal Australian Chemical Institute
Royal Australian
Chemical Institute


 

Article << Previous     |         Contents Vol 66(2)

Eco-Friendly Synthesis of 2-Substituted Benzimidazoles Using Air as the Oxidant

Guo-Feng Chen A D , Hai-Dong Shen A , Hui-Ming Jia A , Li-Yan Zhang A , Hong-Yan Kang A , Qing-Qing Qi A , Bao-Hua Chen B , Jia-Li Cao C and Ji-Tai Li A

A College of Chemistry and Environmental Science, Hebei University, Key Laboratory of Chemical Biology of Hebei Province, Baoding 071002, China.
B College of Pharmaceutical Sciences, Hebei University, Baoding 071002, China.
C Aviation Industry Corporation of China, Beijing Institute of Aeronautical Materials, Beijing 100095, China.
D Corresponding author. Email: chenguofeng@hbu.cn

Australian Journal of Chemistry 66(2) 262-266 http://dx.doi.org/10.1071/CH12458
Submitted: 7 October 2012  Accepted: 5 December 2012   Published: 7 January 2013


 
PDF (249 KB) $25
 Export Citation
 Print
  
Abstract

A simple, environmentally friendly procedure for the synthesis of 2-substituted benzimidazoles by the one-pot condensation of o-phenylenediamines with aromatic aldehydes using continuous bubbling of air in absolute ethanol at room temperature is described. The simplicity of the system, mild conditions, involvement of a non-toxic and practically inexhaustible oxidant, easy and quick isolation of the products, and moderate to good yields are the main advantages of this procedure.





References

[1]  (a) H. Zarrinmayeh, A. M. Nunes, P. L. Ornstein, D. M. Zimmerman, M. B Arnold, D. A. Schober, S. L. Gackenheimer, R. F. Bruns, P. A. Hipskind, T. C. Britton, B. E. Cantrell, D. R. Gehlert, J. Med. Chem. 1998, 41, 2709.
         | CrossRef | CAS |
      (b) A. W. White, R. Almassy, A. Hilary Calvert, N. J. Curtin, R. J. Griffin, Z. Hostomsky, K. Maegley, D. R. Newell, S. Srinivasan, B. T. Golding, J. Med. Chem. 2000, 43, 4084.
         | CrossRef |
      (c) Z. E. Koc, H. Bingol, A. O. Saf, E. Torlak, A. Coskun, J. Hazard. Mater. 2010, 183, 251.
         | CrossRef |
      (d) D. Nannapaneni, V. Gupta Atyam, M. Reddy, S. Raidu, J. Young Pharmacists 2010, 2, 273.
         | CrossRef |

[2]  (a) I. Tamm, Science 1954, 120, 847.
         | CrossRef | CAS |
      (b) M. J. Tebbe, W. A. Spitzer, F. Victor, S. C. Miller, C. C. Lee, T. R. Sattelberg, E. McKinney, C. J. Tang, J. Med. Chem. 1997, 40, 3937.
         | CrossRef |
      (c) T. Roth, M. L. Morningstar, P. L. Boyer, S. H. Hughes, R. W. Buckheit, C. J. Michejda, J. Med. Chem. 1997, 40, 4199.
         | CrossRef |
      (d) A. R. Porcari, R. V. Devivar, L. S. Kucera, J. C. Drach, L. B. Townsend, J. Med. Chem. 1998, 41, 1252.
         | CrossRef |
      (e) M. T. Migawa, J. L. Girardet, J. A. Walker, G. W. Koszalka, S. D. Chamberlain, J. C. Drach, L. B. Townsend, J. Med. Chem. 1998, 41, 1242.
         | CrossRef |
      (f) D. A. Horton, G. T. Bourne, M. L. Smythe, Chem. Rev. 2003, 103, 893.
         | CrossRef |

[3]  Y. J. Bai, J. Lu, Z. Shi, B. Q. Yang, Synlett 2001, 544.
         | CAS |

[4]  (a) J. B. Wright, Chem. Rev. 1951, 48, 397.
         | CrossRef | CAS |
      (b) R. W. Middleton, D. George Wibberley, J. Heterocycl. Chem. 1980, 17, 1757.
         | CrossRef |

[5]  (a) D. W. Hein, R. J. Alheim, J. J. Leavitt, J. Am. Chem. Soc. 1957, 79, 427.
         | CrossRef | CAS |
      (b) A. Czarny, W. D. Wilson, D. W. Boykin, J. Heterocycl. Chem. 1996, 33, 1393.
         | CrossRef |
      (c) R. R. Tidwell, J. D. Geratz, O. Dann, G. Volz, D. Zeh, H. Loewe, J. Med. Chem. 1978, 21, 613.
         | CrossRef |
      (d) T. A. Fairley, R. R. Tidwell, I. Donkor, N. A. Naiman, K. A. Ohemeng, R. J. Lombardy, J. A. Bentley, M. Cory, J. Med. Chem. 1993, 36, 1746.
         | CrossRef |

[6]  (a) K. Bougrin, A. Loupy, M. Soufiaoui, Tetrahedron 1998, 54, 8055.
         | CrossRef | CAS |
      (b) G. Venkat Reddy, V. V. V. N. S. Rama Rao, B. Narsaiah, P. Shanthan Rao, Synth. Commun. 2002, 32, 2467.
         | CrossRef |
      (c) A. Ben-Alloum, S. Bakkas, M. Soufiaoui, Tetrahedron Lett. 1998, 39, 4481.
         | CrossRef |
      (d) G. Navarrete-Vázquez, H. Moreno-Diaz, S. Estrada-Soto, M. Torres-Piedra, I. León-Rivera, H. Tlahuext, O. Muñoz-Muñiz, H. Torres-Gómez, Synth. Commun. 2007, 37, 2815.

[7]  I. Bhatnagar, M. V. George, Tetrahedron 1968, 24, 1293.
         | CrossRef | CAS |

[8]  J. J. Vanden Eynde, F. Delfosse, P. Lor, Y. V. Haverbeke, Tetrahedron 1995, 51, 5813.
         | CrossRef | CAS |

[9]  E. Verner, B. A. Katz, J. R. Spencer, D. Allen, J. Hataye, W. Hruzewicz, H. C. Hui, A. Kolesnikov, Y. Li, C. Luong, A. Martelli, K. Radika, R. Rai, M. She, W. Shrader, P. A. Sprengeler, S. Trapp, J. Wang, W. B. Young, R. L. Mackman, J. Med. Chem. 2001, 44, 2753.
         | CrossRef | CAS |

[10]  A. B. Alloum, K. Bougrin, M. Soufiaoui, Tetrahedron Lett. 2003, 44, 5935.
         | CrossRef |

[11]  L. S. Gadekar, B. R. Arbad, M. K. Lande, Chin. Chem. Lett. 2010, 21, 1053.
         | CrossRef | CAS |

[12]  Y. Kawashita, N. Nakamichi, H. Kawabata, M. Hayashi, Org. Lett. 2003, 5, 3713.
         | CrossRef | CAS |

[13]  M. Curini, F. Epifano, F. Montanari, O. Rosati, S. Taccone, Synlett 2004, 1832.
         | CrossRef | CAS |

[14]  (a) T. Itoh, K. Nagata, H. Ishikawa, A. Ohsawa, Heterocycles 2004, 63, 2769.
         | CrossRef | CAS |
      (b) K. Nagata, T. Itoh, H. Ishikawa, A. Ohsawa, Heterocycles 2003, 61, 93.
         | CrossRef |

[15]  M. Chakrabarty, S. Karmakar, A. Mukherji, S. Arima, Y. Harigaya, Heterocycles 2006, 68, 967.
         | CrossRef | CAS |

[16]  (a) P. Gogoi, D. Konwar, Tetrahedron Lett. 2006, 47, 79.
         | CrossRef | CAS |
      (b) S. Ponnala, D. P. Sahu, Synth. Commun. 2006, 36, 2189.
         | CrossRef |

[17]  M. G. Shen, C. Cai, J. Fluor. Chem. 2007, 128, 232.
         | CrossRef | CAS |

[18]  (a) H. Q. Ma, Y. L. Wang, J. P. Li, J. Y. Wang, Heterocycles 2007, 71, 135.
         | CrossRef | CAS |
      (b) Y. S. Beheshtiha, M. M. Heravi, M. Saeedi, N. Karimi, M. Zakeri, N. Tavakoli-Hossieni, Synth. Commun. 2010, 40, 1216.
         | CrossRef |

[19]  B. Das, H. Holla, Y. Srinivas, Tetrahedron Lett. 2007, 48, 61.
         | CrossRef | CAS |

[20]  L. H. Du, Y. G. Wang, Synthesis 2007, 675.
         | CAS |

[21]  K. Bahrami, M. M. Khodaei, I. Kavianinia, Synthesis 2007, 547.
         | CrossRef | CAS |

[22]  H. Sharghi, O. Asemani, R. Khalifeh, Synth. Commun. 2008, 38, 1128.
         | CrossRef | CAS |

[23]  B. Das, B. S. Kanth, K. R. Reddy, A. S. Kumar, J. Heterocycl. Chem. 2008, 45, 1499.
         | CrossRef | CAS |

[24]  R. Fazaeli, H. Aliyan, Appl. Catal. A Gen. 2009, 353, 74.
         | CrossRef | CAS |

[25]  C. M. Yu, P. Guo, C. Jin, W. K. Su, J. Chem. Res. 2009, 2009, 333.

[26]  B. China Raju, N. Dharma Theja, J. Ashok Kumar, Synth. Commun. 2008, 39, 175.
         | CrossRef |

[27]  K. Bahrami, M. M. Khodaei, F. Naali, Synlett 2009, 569.
         | CrossRef | CAS |

[28]  T. Yamashita, S. Yamada, Y. Yamazaki, H. Tanaka, Synth. Commun. 2009, 39, 2982.
         | CrossRef | CAS |

[29]  J. P. Wan, S. F. Gan, J. M. Wu, Y. J. Pan, Green Chem. 2009, 11, 1633.
         | CrossRef | CAS |

[30]  A. T. Khan, T. Parvin, L. H. Choudhury, Synth. Commun. 2009, 39, 2339.
         | CrossRef | CAS |

[31]  R. V. Shingalapur, K. M. Hosamani, Catal. Lett. 2010, 137, 63.
         | CrossRef | CAS |

[32]  M. Abdollahi-Alibeik, M. Moosavifard, Synth. Commun. 2010, 40, 2686.
         | CrossRef | CAS |

[33]  H. Sharghi, M. H. Beyzavi, M. M. Doroodmand, Eur. J. Org. Chem. 2008, 2008, 4126.
         | CrossRef |

[34]  M. A. Chari, D. Shobha, T. Sasaki, Tetrahedron Lett. 2011, 52, 5575.
         | CrossRef |

[35]  S. N. Lin, L. H. Yang, Tetrahedron Lett. 2005, 46, 4315.
         | CrossRef | CAS |

[36]  G. F. Chen, X. Y. Dong, F. Z. Meng, B. H. Chen, J. T. Li, S. X. Wang, G. Y. Bai, Lett. Org. Chem. 2011, 8, 464.
         | CrossRef | CAS |

[37]  (a) J. T. Li, G. F. Chen, S. X. Wang, H. Lin, T. S. Li, Aust. J. Chem. 2005, 58, 231.
         | CrossRef | CAS |
      (b) D. N. Zhang, J. T. Li, Y. L. Song, G. F. Chen, Lett. Org. Chem. 2011, 8, 385.
         | CrossRef |
      (c) G. Y. Bai, K. Xu, G. F. Chen, Y. H. Yang, T. Y. Li, Synthesis 2011, 1599.
         | CrossRef |
      (d) B. H. Chen, J. T. Li, G. F. Chen, Y. L. Song, Lett. Org. Chem. 2012, 9, 45.
         | CrossRef |
      (e) J. T. Li, Y. W. Li, Y. L. Song, G. F. Chen, Ultrason. Sonochem. 2012, 19, 1.
         | CrossRef |


   
Subscriber Login
Username:
Password:  

 


    
Legal & Privacy | Contact Us | Help

CSIRO

© CSIRO 1996-2015