IJOC  Vol.3 No.2 , June 2013
Al-Pillared Ghassoulite Clay as a New Green Catalyst for the Synthesis of Benzothiazoles and Benzimidazoles: Effect of Amine/CEC Ratio

The following article has been retracted due to the investigation of complaints received against it. The Editorial Board found that substantial portions of the text came from other published papers. The scientific community takes a very strong view on this matter, and the International Journal of Organic Chemistry treats all unethical behavior such as plagiarism seriously. This paper published in Vol.3 No.2, 151-157 (pages), 2013, has been removed from this site.

Title: Al-Pillared Ghassoulite Clay as a New Green Catalyst for the Synthesis of Benzothiazoles and Benzimidazoles: Effect of Amine/CEC Ratio

Authors: Rachid Azzallou, Rachid Mamouni, Kimberly Stieglitz, Nabil Saffaj, Mohammadine Said Lazar

Cite this paper
R. Azzallou, R. Mamouni, K. Stieglitz, N. Saffaj, M. Haddad and S. Lazar, "Al-Pillared Ghassoulite Clay as a New Green Catalyst for the Synthesis of Benzothiazoles and Benzimidazoles: Effect of Amine/CEC Ratio," International Journal of Organic Chemistry, Vol. 3 No. 2, 2013, pp. 151-157. doi: 10.4236/ijoc.2013.32018.
[1]   C. H. Zhou, “Emerging Trends and Challenges in Synthetic Clay-Based Materials and Layered Double Hydroxides,” Applied Clay Science, Vol. 48, No. 1-2, 2010, pp. 1-4. doi:10.1016/j.clay.2009.12.018

[2]   P. Komadel and J. Madejova, “Acid Activation Clay Minerals, Handbook of Clay Science,” Elsevier, Amsterdam, 2006, pp. 263-288. doi:10.1016/S1572-4352(05)01008-1

[3]   F. Belkhadem, A. Maldonado, B. Siebenhaar, J.-M. Clacens, J. M. Perez-Zurita, A. Bengueddach and F. Figueras, “Microalorimetric Measurement of the Acid Properties of Pillared Clays Prepared by Competitive Cation Exchange,” Applied Clay Science, Vol. 39, No. 1-2, 2008, pp. 28-37. doi:10.1016/j.clay.2007.04.005

[4]   R. T. Yang, N. Tharappiwattananon and R. Q. Long, “Ion-Exchanged Pillared Clays for Selective Catalytic Reduction of NO by Ethylene in the Presence of Oxygen,” Applied Catalysis B: Environmental, Vol. 19, No. 3-4, 1998, p. 289.

[5]   C. B. Molina, J. A. Casas, J. A. Zazo and J. J. Rodriguez, “A Comparison of Al-Fe and Zr-Fe Pillared of Clays for Catalytic Wet Peroxide Oxidation,” Chemical Engineering Journal, Vol. 118, No. 1-2, 2006, pp. 29-35. doi:10.1016/j.cej.2006.01.007

[6]   T. J. Pinnavaia, M. Tzou, S. D. Landau and R. H. Raythatha, “On the Pillared and Delamination of Smectite Clay Catalysis by Polyoxo Cations of Aluminium,” Journal of Molecular Catalysis, Vol. 27, No. 1-2, 1984, pp. 195-212. doi:10.1016/0304-5102(84)85080-4

[7]   G. J. J. Bartley and R. Burch, “Zr-Containing Pillared Interlayer Clays. Part III. Influence of Method of Preparation on the Thermal and Hydrothermal Stability,” Applied Catalysis, Vol. 19, No. 1, 1985, pp. 175-185. doi:10.1016/S0166-9834(00)82679-2

[8]   A. Elmchaouri and R. Mahboub, “Effects of Preadsorption of Organic Amine on Al-PILCs Structures,” Colloids and Surfaces A: Physicochemical and Engineering Aspects, Vol. 259, No. 1-3, 2005, pp. 135-141. doi:10.1016/j.colsurfa.2005.02.014

[9]   C. Chen and Y. Chen, “Liquid-Phase Synthesis of 2-Substituted Benzimidazoles, Benzoxazoles and Benzothiazoles,” Tetrahedron Letters, Vol. 45, No. 1, 2004, pp. 113-115. doi:10.1016/j.tetlet.2003.10.095

[10]   N. Siddiqui, A. Rana, S. A. Khan, M. A. Bhat and S. E. Haque, “Synthesis of Benzothiazole Semicarbazones as Novel Anticonvulsants—The Role of Hydrophobic Domain,” Bioorganic & Medicinal Chemistry Letters, Vol. 17, No. 15, 2007, pp. 4178-4182. doi:10.1016/j.bmcl.2007.05.048

[11]   C. J. Lion, C. S. Matthews, G. Wells, T. D. Bradshaw, M. F. G. Stevens and A. D. Westwell, “Antitumour Properties of Fluorinated Benzothiazole-Substituted Hydroxycyclohexa-2,5-Dienones (‘Quinols’),” Bioorganic & Medicinal Chemistry Letters, Vol. 16, No. 19, 2006, pp. 5005-5008. doi:10.1016/j.bmcl.2006.07.072

[12]   S. T. Huang, I. J. Hsei and C. Chen, “Synthesis and Anticancer Evaluation of Bis(benzimidazoles), Bis(benzoxazoles), and Benzothiazoles,” Bioorganic & Medicinal Chemistry Letters, Vol. 14, No. 17, 2006, pp. 6106-6019. doi:10.1016/j.bmc.2006.05.007

[13]   J.-L. Girardet and L. B. Townsend, “Synthesis of β-lLyxofuranosyl Benzimidazoles by an Unexpected Intramolecular Displacement Reaction,” The Journal of Organic Chemistry, Vol. 64, No. 11, 1999, pp. 4169-4172. doi:10.1021/jo981733t

[14]   C.-M. Yeh, C.-L. Tung and C.-M. Sun, “Combinatorial Liquid-Phase Synthesis of Structurally Diverse Benzimidazole Libraries,” Journal of Combinatorial Chemistry, Vol. 2, No. 4, 2000, pp. 341-348. doi:10.1021/cc0000085

[15]   J. J. Chen, Y. Wei, J. C. Drach and L. B. Townsend, “Synthesis and Antiviral Evaluation of Trisubstituted Indole N-Nucleosides as Analogues of 2,5,6-Trichloro-1(beta-D-ribofuranosyl)benzimidazole (TCRB),” Journal of Medicinal Chemistry , Vol. 43, No. 12, 2000, pp. 24492456. doi:10.1021/jm990320x

[16]   D. Tumelty, K. Cao and C. P. Holmes, “Traceless SolidPhase Synthesis of Substituted Benzimidazoles via a Base-Cleavable Linker,” Organic Letters, Vol. 3, No. 1, 2001, pp. 83-86. doi:10.1021/ol006801o

[17]   J. Mann, A. Baron, Y. Opoku-Boahen, E. Johansson, G. Parkinson, L. R. Kelland and S. Neidle, “A New Class of Symmetric Bisbenzimidazole-Based DNA Minor Groove-Binding Agents Showing Antitumor Activity,” Journal of Medicinal Chemistry, Vol. 44, No. 2, 2001, pp. 138-144. doi:10.1021/jm000297b

[18]   B. Raju, N. Nguyen and G. W. Holland, “Solution-Phase Parallel Synthesis of Substituted Benzimidazoles,” Journal of Combinatorial Chemistry, Vol. 4, No. 4, 2002, pp. 320-328. doi:10.1021/cc000098d

[19]   H. Akamatsu, K. Fukase and S. Kusumoto, “New Efficient Route for Solid-Phase Synthesis of Benzimidazole Derivatives,” Journal of Combinatorial Chemistry, Vol. 4, No. 5, 2002, pp. 475-483. doi:10.1021/cc020006f

[20]   C. E. Hoesl, A. Nefzi and 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,” Journal of Combinatorial Chemistry, Vol. 5, No. 2, 2003, pp. 155-160. doi:10.1021/cc020077e

[21]   D. Vourloumis, M. Takahashi, K. B. Simonsen, B. K. Ayida, S. Barluenga, G. C. Winters and T. Hermann, “Solid-Phase Synthesis of Benzimidazole Libraries Biased for RNA Targets,” Tetrahedron Letters, Vol. 44, No. 14, 2003, pp. 2807-2811. doi:10.1016/S0040-4039(03)00453-2

[22]   M.-S. Chua, D.-F. Shi, S. Wrigley, T. D. Bradshaw, I. Hutchinson, P. N. Shaw, D. A. Barrett, L. A. Stanley and M. F. G. Stevens, “Antitumor Benzothiazoles. 7.1 Synthesis of 2-(4-Acylaminophenyl)benzothiazoles and Investigations into the Role of Acetylation in the Antitumor Activities of the Parent Amines,” Journal of Medicinal Chemistry, Vol. 42, No. 3, 1999, pp. 381-392. doi:10.1021/jm981076x

[23]   E. Kashiyama, I. Hutchinson, M.-S. Chua, S. F. Stinson, L. R. Phillips, G. Kaur, E. A. Sausville, T. D. Bradshaw, A. D. Westwell and M. F. G. Stevens, “Antitumor Benzothiazoles. 8.1 Synthesis, Metabolic Formation, and Biological Properties of the Cand N-Oxidation Products of Antitumor 2-(4-aminophenyl)benzothiazoles,” Journal of Medicinal Chemistry, Vol. 42, No. 20, 1999, pp. 41724184. doi:10.1021/jm990104o

[24]   I. Hutchinson, M.-S. Chua, H. L. Browne, V. Trapani, T. D. Bradshaw, A. D. Westwell and M. F. G. Stevens, “Antitumor Benzothiazoles. 14.1 Synthesis and in Vitro Biological Properties of Fluorinated 2-(4-Aminophenyl)benzothiazoles,” Journal of Medicinal Chemistry, Vol. 44, No. 9, 2001, pp. 1446-1455. doi:10.1021/jm001104n

[25]   W. Leng, Y. Zhou and Q. Xu Liu, “Synthesis and Characterization of Nonlinear Optical Side-Chain Polyimides Containing the Benzothiazole Chromophores,” Macromolecules, Vol. 34, No. 14, 2001, pp. 4774-4779. doi:10.1021/ma0100347

[26]   I. Hutchinson, S. A. Jennings, B. R. Vishnuvajjala, A. D. Westwell and M. F. G. Stevens, “Antitumor Benzothiazoles. 16.1 Synthesis and Pharmaceutical Properties of Antitumor 2-(4-Minophenyl)benzothiazole Amino Acid Prodrugs,” Journal of Medicinal Chemistry, Vol. 45, No. 3, 2002, pp. 744-747. doi:10.1021/jm011025r

[27]   F. M. Moghaddam, G. R. Bardajee, H. Ismaili and S. M. “Dokht Taimoory,” Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry, Vol. 36, No. 17, 2006, pp. 2543-2548. doi:10.1080/00397910600781448

[28]   C. Praveen, K. H. Kumar, D. Muralidharan and P. T. Perumal, “Oxidative Cyclization of Thiophenolic and Phenolic Schiff’s Bases Promoted by PCC: A New Oxidant for 2-Substituted Benzothiazoles and Benzoxazoles,” Tetrahedron, Vol. 64, No. 10, 2008, pp. 2369-2374. doi:10.1016/j.tet.2008.01.004

[29]   G. J. Brink, W. C. E. Arends and R. A. Sheldon, “The Baeyer-Villiger Reaction: New Developments toward Greener Procedures,” Chemical Reviews, Vol. 104, No. 9, 2004, pp. 4105-4124. doi:10.1021/cr030011l

[30]   M. Beller, “The Current Status and Future Trends in Oxidation Chemistry,” Advanced Synthesis & Catalysis, Vol. 346, No. 2-3, 2004, pp. 107-108. doi:10.1002/adsc.200404008

[31]   Y. Kawashita, N. Nakamichi, H. Kawabata and M. Hayashi, “Direct and Practical Synthesis of 2-Arylbenzoxazoles Promoted by Activated Carbon,” Organic Letters, Vol. 5, No. 20, 2003, pp. 3713-3715. doi:10.1021/ol035393w

[32]   Y. X. Chen, L. F. Qian, W. Zhang and B. Han, “Efficient Aerobic Oxidative Synthesis of 2-Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4-Methoxy-TEMPO,” Angewandte Chemie International Edition, Vol. 47, No. 48, 2008, pp. 9330-9333. doi:10.1002/anie.200803381

[33]   L. Songnian and Y. Lihu, “A Simple and Efficient Procedure for the Synthesis of Benzimidazoles Using Air as the Oxidant,” Tetrahedron Letters, Vol. 46, No. 25, 2005, pp. 4315-4319. doi:10.1016/j.tetlet.2005.04.101

[34]   Y. Riadi, R. Mamouni, R. Azzalou M.El Haddad, S. Routier, G. Guillaumet and S. Lazar, “An Efficient and Reusable Heterogeneous Catalyst Animal Bone Meal for Facile Synthesis of Benzimidazoles, Benzoxazoles, and Benzothiazoles,” Tetrahedron Letters, Vol. 52, No. 27, 2011, pp. 3492-3495. doi:10.1016/j.tetlet.2011.04.121

[35]   Y. Riadi, R. Mamouni, Y. Abrouki, M. El Haddad, N. Saffaj, S. El Antri, S. Routier, G. Guillaumet and S. Lazar, “Animal Bone Meal (ABM): A Novel Natural Catalyst for Thia-Michael Addition,” Letters in Organic Chemistry, Vol. 7, No. 3, 2010, pp. 269-271. doi:10.2174/157017810791112397

[36]   Y. Riadi, Y. Abrouki, R. Mamouni, M. El Haddad, S. Routier, G. Guillaumet and S. Lazar, “New Eco-Friendly Animal Bone Meal Catalysts for Preparation of Chalcones and Aza-Michael Adducts,” Chemistry Central Journal, Vol. 6, 2012, p. 60.

[37]   R. Azzalou, R. Mamouni, Y. Riady, M. El Haddad, Y. El Mouzdahir, R. Mahboub, A. Elmchaouri, S. Lazar and G. Guillaumet, “A Mild and Efficient One-Pot Synthesis of 2-Substituted Benzimidazoles through a New Surfactant-Modified Moroccan Clay Catalyst,” Revista de Chimie (Bucharest), Vol. 61, No. 12, 2010, pp. 11551157.

[38]   R. Azzalou, R. Mamouni, M. El Haddad, M. C. ViaudMassuard, G. Guillaumet and S. Lazar, “Optimization of the Synthesis of 2-Substituted Benzimidazoles Catalyzed by Al-PILC Under Microwave Irradiation,” Revista de Chimie, Vol. 62, 2011, p. 2.

[39]   R. Glaeser, “Determination of the Base-Exchange Capacity in Montmorillonite,” Comptes Rendus de l’Académie des Sciences de Paris, Vol. 222, 1946, p. 1179.

[40]   E. P. Barrett, L. G. Joyner and P. H. Halenda, “The Determination of Pore Volume and Area Distributions in Porous Substances. I. Computations from Nitrogen Isotherms,” Journal of the American Chemical Society, Vol. 73, No. 1, 1951, pp. 373-380. doi:10.1021/ja01145a126

[41]   V. R. Devalla and K. Ethirajulu, “Synthesis of 2-Substituted Benzoxazoles and Benzimidazoles Based on Mass Spectral Ortho Interactions,” Journal of the Chemical Society, Perkin Transactions 2, No. 7, 1995, pp. 1497-1501.

[42]   H. Thakuria and G. Das, “An Expeditious One-Pot Solvent-Free Synthesis of Benzimidazole Derivatives,” Archive for Organic Chemistry, Vol. 2008, No. 15, 2008, pp. 321-328. doi:10.3998/ark.5550190.0009.f28

[43]   K. Bougrin, A. Loupy and M. Soufiaoui, “Trois Nouvelles Voies de Synthèse des Dérivés 1,3-Azoliques Sous Micro-Ondes,” Tetrahedron, Vol. 54, No. 28, 1998, pp. 8055-8064. doi:10.1016/S0040-4020(98)00431-1

[44]   S. L. Balaji, R. P. Umesh, R. M. Jyotirling and A. M. Ramrao, “Synthesis of 2-Arylbenzothiazoles Catalyzed by Biomimetic Catalyst, β-Cyclodextrin,” Bulletin of the Korean Chemical Society, Vol. 31, No. 8, 2010, pp. 23292332. doi:10.5012/bkcs.2010.31.8.2329

[45]   K. M. Khan, F. Rahim, S. A. Halim, M. Taha, M. Khan, S. Perveen, Z. Haq, M. A. Mesaik and M. I. Choudhary, “Synthesis of Novel Inhibitors of β-Glucuronidase Based on Benzothiazole Skeleton and Study of Their Binding Affinity by Molecular Docking,” Bioorganic & Medicinal Chemistry, Vol. 19, No. 14, 2011, pp. 4286-4294. doi:10.1016/j.bmc.2011.05.052