Facile and convenient new synthesis of imidazobenzimidazol-2-one and pyrimidobenzimidazol-2,3-dione derivatives

Authors

  • Abdelkebir Zarguil Laboratoire de Synthèse Organique, Organométallique et Théorique, Département de Chimie, Faculté des Sciences, Université Ibn Tofaïl, Kénitra, Maroc.
  • Mohammed Saadouni Laboratoire de Synthèse Organique, Organométallique et Théorique, Département de Chimie, Faculté des Sciences, Université Ibn Tofaïl, Kénitra, Maroc.
  • Said Boukhris Laboratoire de Synthèse Organique, Organométallique et Théorique, Département de Chimie, Faculté des Sciences, Université Ibn Tofaïl, Kénitra, Maroc.
  • Nouzha Habbadi Laboratoire de Synthèse Organique, Organométallique et Théorique, Département de Chimie, Faculté des Sciences, Université Ibn Tofaïl, Kénitra, Maroc.
  • Amina Hassikou Laboratoire de Synthèse Organique, Organométallique et Théorique, Département de Chimie, Faculté des Sciences, Université Ibn Tofaïl, Kénitra, Maroc.
  • Abdelaziz Souizi Laboratoire de Synthèse Organique, Organométallique et Théorique, Département de Chimie, Faculté des Sciences, Université Ibn Tofaïl, Kénitra, Maroc.

DOI:

https://doi.org/10.13171/mjc.1.1.2011.10.06.18

Abstract

 Reaction of epoxides 1 and 2 with 2-aminobenzimidazole led to formation of imidazobenzimidazol-2-ones 4 and pyrimido[1,2-a]benzimidazol-2,3-diones 5, respectively in good yields. This same compound 5 may be obtained by another route by reacting halohydrin derivates 3 with 2-aminobenzimidazole. The mechanisms of the studied reactions are discussed.

References

- P. K. Dubey, P. V. V. Prasada Reddy, K. Srinivas, Arkivoc, 2007, XV, 192-198 and cited references.

- K. Karen, Antiviral. Biron. Antiviral Res., 2006, 71, 154-163.

- R. Paramashivappa, P. Phani Kumar, P. V. Subba Rao, A. Srinivasa Rao, Bioorg. Med. Chem. Lett., 2003, 13, 657-660.

- C. Palcy, A. Silvestre, C. Sauve, J. Cortet, J. Cabaret, The Veterinary Journal, 2010, 183, 68-74.

- Y. F. Li, G. F. Wang, Y. Luo, W. G. Huang, W. Tang, C. L. Feng, L. P. Shi, Y. D. Ren, J. P. Zuo, W. Lu, Eur. J. Med. Chem., 2007, 42, 1358-1364.

- W.B. Young, P. Sprengeler, W. D. Shrader, Y. Li, R. Rai, E. Verner, T. Jenkins, P. Fatheree, A. Kolesnikov, J. W. Janc, L. Cregar, K. Elrod, B. Katz, Bioorg. Med. Chem. Lett., 2006, 16, 710-713.

- P. A. Thakurdesai, S. G. Wadodkar, C. T. Chopade, Pharmacologyonline 1, 2007, 314-329.

- R. Vinodkumar, S. D. Vaidya, B. V. Siva Kumar, U. N. Bhise, S. B. Bhirud, U. C. Mashelkar, Eur. J. Med. Chem., 2008, 43, 986-995.

- a) M. M Ramla, M. A. Omar, H. Tokuda, H. I. El Diwani, Bioorg. Med. Chem., 2007, 15, 6489-6496. b) A. Gellis, H. Kovacic, N. Boufatah, P. Vanelle, European Journal of Medicinal Chemistry, 2008, 43, 1858-1864.

- A. A. O. Sarhan, A. Al-Dhfyan, M. A. Al-Mozaini, C. N. Adra, T. Aboul-Fadl, European Journal of Medicinal Chemistry, 2010, 45, 2689-2694. 11 - a) K. F. Ansari, C. Lal, European Journal of Medicinal Chemistry, 2009, 44, 4028-4033. b) M. Tunçbilek, T. Kiper, N. Altanlar, European Journal of Medicinal Chemistry, 2009, 44, 1024-1033.

- a) P. T. M. Nguyen, J. D. Baldeck, J. Olsson, R. E. Marquis, Oral Microbiol. Immunol., 2005, 20, 93-100. b) M. Boiani, M. Gonzalez, Mini Rev. Med. Chem., 2005, 5, 409-424. c) S. Ozden, D. Atabey, S. Yıldız, H. Göker, Bioorg. Med. Chem., 2005, 13, 1587-1597. d) H. Göker, S. Ozden, S. Yıldız, D. W. Boykin, Eur. J. Med. Chem., 2005, 40, 1062-1069.

- L. M. Werbel, A. Curry, E. Elslarger, C. A. Hess, M. P. Hutt, C. J. Youngstrom, Heterocycl. Chem., 1969, 6, 787-796. 14 - A. Abdel-monem, A. Abdel-hafez, Arch. Pharm. Res., 2007, 30, 678-684.

- G. Ayhan-Kilcigil, C. Kus, E. D. Ozdamar, B. Can-Eke, M. Iscan, Arch. Pharm., 2007, 34, 607-611

- R. V. Shingalapur, K. M. Hosamani, R. S. Keri, M. H. Hugar, European Journal of Medicinal Chemistry, 2010, 45, 1753-1759.

- J. R. Hwu, R. Singha, S. C. Hong, Y. H. Chang, A. R. Das, I. Vliegen, E. De Clercq, J. Neyts, Antiviral Research, 2008, 77, 157-162

- N. M. Elwan, Tetrahedron, 2004, 60, 1161-1166 and cited references.

- a) A. Gaz, F. Ammadi, S. Boukhris, A. Souizi, G. Coudert, J. Heterocycl. Chem., 1999, 5, 413-417. b) F. Ammadi, S. Boukhris, A. Souizi, G. Coudert, Tetrahedron Lett., 1999, 40, 6517-6518

- A. Zarguil, S. Boukhris , M. L. El Efrit , A. Souizi , E. M. Essassi, Tetrahedron Lett., 2008, 49, 5883-5886

- H. Wahe, P. F. Asobo, R. A. Cherkasov, Z. T. Fomum, D. Doepp, Arkivoc, 2004, I, 130-137 and cited references.

- A. Oulad Yakhlef, S. Boukhris, A. Souizi, A. Robert, Bull. Soc. Chim. Fr., 1997, 134, 111-113.

- a) S. Boukhris, A. Souizi, A. Robert, Tetrahedron Lett., 1996, 37 (27), 4693-4696. b) S. Boukhris, A. Souizi, A. Robert, Tetrahedron Lett., 1998, 39, 6281-6282. c) S. Boukhris, A. Souizi, Tetrahedron Lett., 2003, 44, 3259-3261.

- M. H. Elnagdi, H. Wamhoff, J. Heterocycl. Chem., 1981, 18, 1287-1292.

- D. Hurtaud, M. Baudy-Floc’h, A. Robert, J. Le Grel, J. Org. Chem., 1978, 43, 3732-3740 and cited references.

Downloads

Published

2011-06-10

Issue

Vol. 1 No. 1 (2011)

Section

Organic Chemistry

License

Authors who publish with this journal agree to the following terms:

    1. Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal
    2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal
    3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).