Calcined Mussel Shells Doped with Metal Halides as a Novel Catalyst for the Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles

Meryem Hamlich; Souad Harkati; Yassine Riadi; Rachid Slimani; Lakhmiri Rajae; Said Lazar; Mohamed Safi

doi:doi:10.11648/j.ijbc.20170203.21

| Peer-Reviewed

Calcined Mussel Shells Doped with Metal Halides as a Novel Catalyst for the Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles

Meryem Hamlich, Souad Harkati, Yassine Riadi, Rachid Slimani, Lakhmiri Rajae, Said Lazar, Mohamed Safi

Published in International Journal of Bioorganic Chemistry (Volume 2, Issue 3)

Received: 9 March 2017 Accepted: 20 March 2017 Published: 16 May 2017

Views: Downloads:

Download PDF

Share This Article

Twitter
Linked In
Facebook

Abstract

Calcined Mussel Shells (CMS) doped with ZnCl₂ are an efficient natural, accessible and reusable catalyst for the synthesis of benzimidazoles, benzoxazoles and benzothiazoles using o-phenylenediamine, o-aminophenol and o-aminothiophenol with different aldehydes. Their actions were conducted under reflux conditions in the air. The procedure is very simple with good to excellent yields in a short reaction time, easy purification. The catalyst can be recycled effectively after used.

Published in	International Journal of Bioorganic Chemistry (Volume 2, Issue 3)
DOI	10.11648/j.ijbc.20170203.21
Page(s)	153-158
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2017. Published by Science Publishing Group

Keywords

Calcined Mussel Shells (CMS), Heterogeneous Catalysis, Benzimidazoles, Benzoxazoles, Benzothiazoles, Green Chemistry

References

[1]	M. R. Grimmett, “Imidazole and Benzimidazole Synthesis, ”Academic Press Inc, 1997.
[2]	A. Bhatnagar, P. K. Sharma, N. A. Kumar, “A review on Imidazoles: their chemistry and pharmacological potentials,” Int. J. Pharm Tech Res, vol. 3, pp. 268-282, 2011.
[3]	R. J. Sundberg, R. B. Martin, “Interactions of histidine and other imidazole derivatives with transition metal ions in chemical and biological systems,”Chem. Rev, vol.74, pp. 471-517, 1974.
[4]	C. Chen, Y. J. Chen, “Liquid-phase synthesis of 2-substituted benzimidazoles, benzoxazoles and benzothiazoles,” Tetrahedron. Lett, vol. 45, pp. 113-115, 2004.
[5]	X. Song, B. S. Vig, P. L. Lorenzi, J. C. Drach, L. B. Townsend, G. L. Amidon, “Amino acid ester prodrugs of the antiviral agent 2-bromo-5,6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole as potential substrates of PEPT1transporter,” J. Med. Chem, vol. 48, pp. 1274-1277, 2005.
[6]	Y. Yildiz, I. Yalcin, E. Aki-Sener, N. Ucarturk, “Synthesis and structure-activity relationships of new antimicrobial active multisubstituted benzazole derivatives,”Eur. J. Med. Chem, vol. 39, pp. 291-298, 2004.
[7]	M. Yamato, “Study on the development of biological-active compounds after the model of natural products,” J. Pharm. Soc. Jpn, vol. 112, pp. 81-99, 1992.
[8]	A. Benazzouz, T. Boraud, P. Dubedat, A. Boireau, J. M. Stutzmann, C. Gross, “Riluzole prevents MPTP-induced parkinsonism in the rhesus monkey: a pilot study,” Eur. J. Pharmacol, vol. 284, pp. 299-307, 1995.
[9]	D. Kumar, M. R. Jacob, M. B. Reynolds, S. M. Kerwin, “Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1,” Bioorg. Med. Chem, vol. 10, pp. 3997-4004, 2002.
[10]	D. A. Evans, C. E. Sacks, W. A. Kleschick, T. R. Taber, “Polyether antibiotics synthesis. Total synthesis and absolute configuration of the ionophore A-23187,” J. Am. Chem. Soc, vol. 101, pp. 6789-6791, 1979.
[11]	A. Figge, H. J. Altenbach, D. J. Brauer, P. Tielmann, “Synthesis and resolution of 2-(2-diphenylphosphinyl-naphthalen-1-yl)-1-isopropyl-1H-benzoimidazole; a new atropisomeric P, N-chelating ligand for asymmetric catalysis,” Tetrahedron Asymmetry, vol.13, pp. 137-144, 2002.
[12]	S. T. Huang, I. J. Hsei, C. Chen, “Synthesis and anticancer evaluation of bis (benzimidazoles), bis (benzoxazoles), and benzothiazoles,” Bioorg. Med. Chem, vol. 14, pp. 6106-6119, 2006.
[13]	J. L. Girardet, L. B. Townsend, “Synthesis of β-1-lyxofuranosyl benzimidazoles by an unexpected intramolecular displacement reaction,” J. Org. Chem, vol. 64, pp. 4169-4172, 1999.
[14]	C. M. Yeh, C. L. Tung, C. M. Sun, “Combinatorial liquid-phase synthesis of structurally diverse benzimidazole libraries,” J. Comb. Chem, vol. 2, pp. 341-348, 2000.
[15]	J. J. Chen, V. Wie, J. C. Drach, L. B. Townsend, “Synthesis and antiviral evaluation of trisubstitutedindoleN-Nucleosides as analogues of 2, 5, 6-trichloro-1-(β-d-ribofuranosyl)benzimidazole (TCRB),” J. Med. Chem, vol. 43, pp. 2449-2456, 2000.
[16]	D. Tumelty, K. Cao, C. P. Holmes, “Traceless solid-phase synthesis of substituted benzimidazoles via a base-cleavable linker,” Org. Lett, vol. 3, pp. 83-86, 2001.
[17]	J. Mann, A. Baron, Y. Opoku-Boahen, E. Johansson, G. Parkinson, L. R. Kelland, S. Neidle, “A new class of symmetric bis benzimidazole-based DNA minor groove-binding agents showing antitumor activity,” J. Med. Chem, vol. 44, pp. 138-144, 2001.
[18]	B. Raju, N. Nguyen, G. W. Holland, “Solution-phase parallel synthesis of substituted benzimidazoles,” J. Comb. Chem.4, 320-328, 2002.
[19]	H. Akamatsu, K. Fukase, S. Kusumoto, New efficient route for solid-phase synthesis of benzimidazole derivatives,” J. Comb. Chem, vol. 4, pp. 475-483, 2002.
[20]	C. E. Hoesl, A. Nefzi, R. A. Houghten, “Parallel solid-phase synthesis of 2-imino-4-oxo-1, 3, 5-triazino [1, 2-a]benzimidazoles via tandem aza-wittig/heterocumulene-mediated annulation reaction,” J. Comb. Chem, vol. 5, pp. 155-160, 2003.
[21]	D. Vourloumis, M. Takahashi, K. B. Simonsen, B. K. Ayida, S. Barluenga, G. C. Winters, T. Hermann, “Solid-phase synthesis of benzimidazole libraries biased for RNA targets,” Tetrahedron Lett, vol. 44, pp. 2807-2811, 2003.
[22]	N. H. Cano, J. G. Uranga, M. Nardi, A. Procopio, D. A. Wunderlin and A. N. Santiago, “Selective and eco-friendly procedures for the synthesis of benzimidazoles derivatives. The role of the Er (OTf)3 catalyst in the reaction selectivity”, Beilstein J. Org. Chem. 2016, 12, 2410–2419.
[23]	D. F. Shi, T. D. Bradshaw, S. Wrigley, C. J. McCall, P., Lelieveld, I. Fichtner, M. F. G. Stevens, “Antitumor benzothiazoles. Synthesis of 2-(4-aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo,” J. Med. Chem, vol. 39, pp. 3375-3384, 1996.
[24]	X. Beebe, D. Wodka, T. J. Sowin, “Solid-phase synthesis of benzoxazoles from 3-nitrotyrosine,” J. Comb. Chem, vol. 3, pp. 360-366, 2001.
[25]	A. Hari, C. Karan, W. C. Rodrigues, B. L. Miller, “Extending the scope of chromium-manganese redox-coupled reactions: a one-pot synthesis of benzoxazoles,” J. Org. Chem, vol. 66, pp. 991-996, 2001.
[26]	R. S. Pottorf, N. K. Chadha, M. Katkevics, V. Ozola, E. Suna, H. Ghane, T. Regberg, M. R. Player, “Parallel synthesis via microwave-assisted dielectric heating,” Tetrahedron Lett, vol. 44, pp. 175-178, 2003.
[27]	F. Chen, C. Shen, D. Yang, “A simple protocol for the synthesis of 2-arylbenzoxazoles by oxidation with o-iodoxybenzoic acid (IBX) and its application in the synthesis of arylbenzoxazole-containing amino acids,” Tetrahedron Lett, vol. 52, pp. 2128-2131, 2011.
[28]	M. S. Chua, D. F. Shi, S. Wrigley, T. D. Bradshaw, I. Hutchinson, P. N. Shaw, D. A. Barrett, L. A. Stanley, M. F. G. Stevens, “Antitumor benzothiazoles. Synthesis of 2-(4-acylaminophyl)benzothiazoles and investigations into the role of acetylation in the antitumor activities of the parent amines,” J. Med. Chem, vol. 42, pp. 381-392, 1999.
[29]	E. Kashiyama, I. Hutchinson, M. S. Chua, S. F. Stinson, L. R. Phillips, G. Kaur, E. A. Sausville, T. D. Bradshaw, A. D. Westwell, M. F. G. Stevens, “Antitumor benzothiazoles. Synthesis, metabolic formation, a, d biological properties of the C- and N- oxidation products of antitumor 2-(4-aminophenyl)benzothiazoles,” J. Med. Chem, vol. 42, pp. 4172-4184, 1999.
[30]	I. Hutchinson, M. S. Chua, H. L. Browne, V. Trapani, T. D. Bradshaw, A. D. Westwell, M. F. G. Stevens, “Antitumor benzothiazoles. Synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl)benzothiazoles,” J. Med. Chem, vol. 44, pp. 1446-1455, 2001.
[31]	W. Leng, Y. Zhou, O. Xu, J. Liu, “Synthesis and characterization of nonlinear optical side-chain polyimides containing the benzothiazolechromophores,” Macromolecules, vol. 34, pp. 4774-4779, 2001.
[32]	I. Hutchinson, S. A. Jennings, B. R. Vishnuvajjala, A. D. Westwell, M. F. G. “Stevens, Antitumor benzothiazoles. Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazoleaminoacid prodrugs,” J. Med. Chem, vol. 45, pp. 744-747, 2002.
[33]	Y. Riadi, R. Mamouni, Y. Abrouki, M. Elhaddad, N. Saffaj, S. ElAntri, S. Routier, G. Guillaumet, S. Lazar, “Animal bone meal (ABM): A novel natural catalyst for thia-michael addition,” Lett. Org. Chem, vol.7, pp. 269-271, 2010.
[34]	Y. Riadi, R. Mamouni, R. Azzalou, R. Boulahjar, Y. Abrouki, M. Elhaddad, S. Routier, G. Guillaumet, S. Lazar, “Animal bone meal as an efficient catalyst for crossed-aldolcondensation,” Tetrahedron Lett, vol. 51, pp. 6715-6717, 2010.
[35]	Y. Riadi, R. Mamouni, R. Azzalou, M. Elhaddad, S. Routier, G. Guillaumet, S. Lazar, “An efficient and reusable heterogeneous catalyst animal bone meal for facile synthesis of benzimidazoles, benzoxazoles, and benzothiazoles,” Tetrahedron Lett, vol. 52, pp. 3492-3495, 2011.
[36]	Y. Riadi, Y. Abrouki, R. Mamouni, M. Elhaddad, S. Routier, G. Guillaumet, S. Lazar, “New eco-friendly animal meal catalysts for preparation of chalcones and aza-michael adducts,” Chem. Cent. J, vol. 6, pp. 60-66, 2012.
[37]	Y. Riadi, R. Slimani, A. Haboub, S. Elantri, M. Safi, S. Lazar, “Calcined eggshell meal: new solid support for the knoevenagel reaction in heterogeneous media,” Mor. J. Chem, vol. 1, pp. 24-28, 2013.
[38]	L. Songnian, Y. Lihu, “A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant,” Tetrahedron Lett, vol. 46, pp. 4315-4319, 2005.
[39]	K. Bougrin, A. Loupy, M. Soufiaoui, “Trois nouvelles voies de synthèse des dérivés 1,3-azoliques sous micro-ondes,” Tetrahedron, vol. 54, pp. 8055-8064, 1998.
[40]	S. L. Balaji, R. P. Umesh, R. M. Jyotirling, A. M. Ramrao, “Synthesis of 2-arylbenzothiazoles catalyzed by biomimetic catalyst, β-cyclodextrin Bull.” Korean Chem. Soc, vol. 31, pp. 2329-2332, 2010.
[41]	A. Haboub, M. Hamlich, S. Harkati, Y. Riadi, R. Slimani, M. Aadil, A. Anouzla, S. Lazar, M. Safi, “New methodologie eco-friendly using calcined eggshell meal catalyst for synthesis of benzimidazoles, benzoxazoles and benzothiazoles,” Am. J. Env. Prot, vol. 4, pp. 28-32, 2015.
[42]	S. Harkati, M. Hamlich, F. Echabbi, Y. Riadi, R. Slimani, K. Halim, S. Lazar, M. Safi, “Calcined limpet shell: new solid support for an easy synthesis of benzimidazoles, benzoxazoles and benzothiazoles in heterogeneous media,” J. Mar. Chim. Heterocycl, vol. 15, pp. 32-40, 2016.
[43]	M. Hamlich, S. Harkati, S. Lazar, M. Safi, Y. Riadi, “A novel green synthesis of pyrimidinone derivatives via Biginelli reaction using Animal Bone Meal as catalyst.,” J. Mat. Env. Scien, vol. 7, pp. 4692-4696, 2016.

Cite This Article

Plain Text BibTeX RIS

APA Style

Meryem Hamlich, Souad Harkati, Yassine Riadi, Rachid Slimani, Lakhmiri Rajae, et al. (2017). Calcined Mussel Shells Doped with Metal Halides as a Novel Catalyst for the Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles. International Journal of Bioorganic Chemistry, 2(3), 153-158. https://doi.org/10.11648/j.ijbc.20170203.21

Copy | Download

ACS Style

Meryem Hamlich; Souad Harkati; Yassine Riadi; Rachid Slimani; Lakhmiri Rajae, et al. Calcined Mussel Shells Doped with Metal Halides as a Novel Catalyst for the Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles. Int. J. Bioorg. Chem. 2017, 2(3), 153-158. doi: 10.11648/j.ijbc.20170203.21

Copy | Download

AMA Style

Meryem Hamlich, Souad Harkati, Yassine Riadi, Rachid Slimani, Lakhmiri Rajae, et al. Calcined Mussel Shells Doped with Metal Halides as a Novel Catalyst for the Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles. Int J Bioorg Chem. 2017;2(3):153-158. doi: 10.11648/j.ijbc.20170203.21

Copy | Download

@article{10.11648/j.ijbc.20170203.21,
  author = {Meryem Hamlich and Souad Harkati and Yassine Riadi and Rachid Slimani and Lakhmiri Rajae and Said Lazar and Mohamed Safi},
  title = {Calcined Mussel Shells Doped with Metal Halides as a Novel Catalyst for the Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles},
  journal = {International Journal of Bioorganic Chemistry},
  volume = {2},
  number = {3},
  pages = {153-158},
  doi = {10.11648/j.ijbc.20170203.21},
  url = {https://doi.org/10.11648/j.ijbc.20170203.21},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijbc.20170203.21},
  abstract = {Calcined Mussel Shells (CMS) doped with ZnCl2 are an efficient natural, accessible and reusable catalyst for the synthesis of benzimidazoles, benzoxazoles and benzothiazoles using o-phenylenediamine, o-aminophenol and o-aminothiophenol with different aldehydes. Their actions were conducted under reflux conditions in the air. The procedure is very simple with good to excellent yields in a short reaction time, easy purification. The catalyst can be recycled effectively after used.},
 year = {2017}
}

Copy | Download

TY  - JOUR
T1  - Calcined Mussel Shells Doped with Metal Halides as a Novel Catalyst for the Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles
AU  - Meryem Hamlich
AU  - Souad Harkati
AU  - Yassine Riadi
AU  - Rachid Slimani
AU  - Lakhmiri Rajae
AU  - Said Lazar
AU  - Mohamed Safi
Y1  - 2017/05/16
PY  - 2017
N1  - https://doi.org/10.11648/j.ijbc.20170203.21
DO  - 10.11648/j.ijbc.20170203.21
T2  - International Journal of Bioorganic Chemistry
JF  - International Journal of Bioorganic Chemistry
JO  - International Journal of Bioorganic Chemistry
SP  - 153
EP  - 158
PB  - Science Publishing Group
SN  - 2578-9392
UR  - https://doi.org/10.11648/j.ijbc.20170203.21
AB  - Calcined Mussel Shells (CMS) doped with ZnCl2 are an efficient natural, accessible and reusable catalyst for the synthesis of benzimidazoles, benzoxazoles and benzothiazoles using o-phenylenediamine, o-aminophenol and o-aminothiophenol with different aldehydes. Their actions were conducted under reflux conditions in the air. The procedure is very simple with good to excellent yields in a short reaction time, easy purification. The catalyst can be recycled effectively after used.
VL  - 2
IS  - 3
ER  -

Copy | Download

Author Information

Meryem Hamlich

Laboratory of Physical Chemistry and Bioorganic Chemistry, Faculty of Sciences and Techniques, University Hassan II, Mohammedia, Morocco
Souad Harkati

Laboratory of Physical Chemistry and Bioorganic Chemistry, Faculty of Sciences and Techniques, University Hassan II, Mohammedia, Morocco
Yassine Riadi

Department of Pharmaceutical Chemistry, College of Pharmacy, University Sattam Bin Abdulaziz, Alkharj, Saudi Arabia
Rachid Slimani

Laboratory Biochemistry, Environment and Agri-Food, Faculty of Sciences and Techniques, University Hassan II, Mohammedia, Morocco
Lakhmiri Rajae

Laboratory of Materials and Valorization of the Resources, Faculty of Sciences and Techniques, University Abdelmalek Essaadi, Tangier, Morocco
Said Lazar

Laboratory Biochemistry, Environment and Agri-Food, Faculty of Sciences and Techniques, University Hassan II, Mohammedia, Morocco
Mohamed Safi

Laboratory of Physical Chemistry and Bioorganic Chemistry, Faculty of Sciences and Techniques, University Hassan II, Mohammedia, Morocco

Download PDF

Sections

Plain Text BibTeX RIS

APA Style

Meryem Hamlich, Souad Harkati, Yassine Riadi, Rachid Slimani, Lakhmiri Rajae, et al. (2017). Calcined Mussel Shells Doped with Metal Halides as a Novel Catalyst for the Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles. International Journal of Bioorganic Chemistry, 2(3), 153-158. https://doi.org/10.11648/j.ijbc.20170203.21

Copy | Download

ACS Style

Meryem Hamlich; Souad Harkati; Yassine Riadi; Rachid Slimani; Lakhmiri Rajae, et al. Calcined Mussel Shells Doped with Metal Halides as a Novel Catalyst for the Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles. Int. J. Bioorg. Chem. 2017, 2(3), 153-158. doi: 10.11648/j.ijbc.20170203.21

Copy | Download

AMA Style

Meryem Hamlich, Souad Harkati, Yassine Riadi, Rachid Slimani, Lakhmiri Rajae, et al. Calcined Mussel Shells Doped with Metal Halides as a Novel Catalyst for the Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles. Int J Bioorg Chem. 2017;2(3):153-158. doi: 10.11648/j.ijbc.20170203.21

Copy | Download

@article{10.11648/j.ijbc.20170203.21,
  author = {Meryem Hamlich and Souad Harkati and Yassine Riadi and Rachid Slimani and Lakhmiri Rajae and Said Lazar and Mohamed Safi},
  title = {Calcined Mussel Shells Doped with Metal Halides as a Novel Catalyst for the Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles},
  journal = {International Journal of Bioorganic Chemistry},
  volume = {2},
  number = {3},
  pages = {153-158},
  doi = {10.11648/j.ijbc.20170203.21},
  url = {https://doi.org/10.11648/j.ijbc.20170203.21},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijbc.20170203.21},
  abstract = {Calcined Mussel Shells (CMS) doped with ZnCl2 are an efficient natural, accessible and reusable catalyst for the synthesis of benzimidazoles, benzoxazoles and benzothiazoles using o-phenylenediamine, o-aminophenol and o-aminothiophenol with different aldehydes. Their actions were conducted under reflux conditions in the air. The procedure is very simple with good to excellent yields in a short reaction time, easy purification. The catalyst can be recycled effectively after used.},
 year = {2017}
}

Copy | Download

TY  - JOUR
T1  - Calcined Mussel Shells Doped with Metal Halides as a Novel Catalyst for the Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles
AU  - Meryem Hamlich
AU  - Souad Harkati
AU  - Yassine Riadi
AU  - Rachid Slimani
AU  - Lakhmiri Rajae
AU  - Said Lazar
AU  - Mohamed Safi
Y1  - 2017/05/16
PY  - 2017
N1  - https://doi.org/10.11648/j.ijbc.20170203.21
DO  - 10.11648/j.ijbc.20170203.21
T2  - International Journal of Bioorganic Chemistry
JF  - International Journal of Bioorganic Chemistry
JO  - International Journal of Bioorganic Chemistry
SP  - 153
EP  - 158
PB  - Science Publishing Group
SN  - 2578-9392
UR  - https://doi.org/10.11648/j.ijbc.20170203.21
AB  - Calcined Mussel Shells (CMS) doped with ZnCl2 are an efficient natural, accessible and reusable catalyst for the synthesis of benzimidazoles, benzoxazoles and benzothiazoles using o-phenylenediamine, o-aminophenol and o-aminothiophenol with different aldehydes. Their actions were conducted under reflux conditions in the air. The procedure is very simple with good to excellent yields in a short reaction time, easy purification. The catalyst can be recycled effectively after used.
VL  - 2
IS  - 3
ER  -

Copy | Download