Valorization of the Phosphate Fertilizers Catalytic Activity in 1-(Benzothiazolylamino) Methy l-2-Naphthol Derivatives Synthesis
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The present work focused on developing a new protocol of the 1-(benzothiazolylamino) methyl-2-naphthol derivatives synthesis by condensation of three compounds, i.e. aromatic 2-naphthol, 2-aminobenzothiazole and aldehyde. Furthermore, this reaction was carried out in the presence of three heterogeneous phosphate catalysts: monoammonium phosphates (MAP), diammonium phosphate (DAP), and trisuperphosphate (TSP). Moreover, this method offered many advantages, such as: very high yields, shorter reaction times, and the catalysts, can be easily recovered and reused without any loss of their catalytic activities. Copyright ©2019 BCREC Group. All rights reserved
Received: 19th July 2018; Revised: 27th October 2018; Accepted: 4th November 2018; Available online: 8th April 2019; Published regularly: 1st August 2019
How to Cite: Zimou, O., Malek, B., Elhallaoui, A., Ghailane, T., Ghailane, R., Boukhris, S., Habbadi, N., Hassikou, A., Souizi, A. (2019). Valorization of the Phosphate Fertilizers Catalytic Activity in 1-(Benzothiazolylamino) Methy l-2-Naphthol Derivatives Synthesis. Bulletin of Chemical Reaction Engineering & Catalysis, 14 (2): xxx-xxx (doi:10.9767/bcrec.14.2.2976.xxx-xxx)
- Xu, L. W., Xia, C. G., Li, L. (2004). Transition Metal Salt-Catalyzed DirectThree-Component Mannich Reactions of Aldehydes, Ketones, and Carbamates: Efficient Synthesis of N-Protected β-Aryl-β-Amino Ketone Compounds. J Org Chem, 69: 8482‑8484.
- Dömling, A. (2006). Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry. Chem Rev, 106: 17‑89.
- Katritzky, A.R., Tymoshenko, D.O., Monteux, D., Vvedensky, V., Nikonov, G., Cooper, C.B., Deshpande, M. (2000). A New Three-Carbon Synthon for Efficient Synthesis of Benzannelated and 1-(2-Arylethenyl) Heterocycles. J Org Chem, 65: 8059‑8062.
- El-Shorbagi, A. N., Sakai, S., El-Gendy, M.A., Omar, N., Farag, H. H. (1989). Imidazo(2,1-b)benzothiazoles. II. Synthesis and antiinflammatory activity of some imidazo(2,1-b)benzothiazoles. Chem Pharm Bull, 37: 2971‑2975.
- Yang, X., Liang, J. (2011). 1,3-Dibromo-5,5-dimethylhydantoin catalyzed one-pot synthesis of 2-arylbenzothiazoles. Collect Czechoslov Chem Commun, 76: 1909‑1915.
- Palkar, M., Noolvi, M., Sankangoud, R., Maddi, V., Gadad, A., Nargund, L.V. G. (2010). Synthesis and Antibacterial Activity of a Novel Series of 2,3-Diaryl-substituted-imidazo(2,1-b) benzothiazole Derivatives. Arch Pharm, 343: 353‑359.
- Chopade, R.S., Bahekar, R.H., Khedekar, P.B., Bhusari, K.P., Ram Rao, A. R. (2002). Synthesis and Anticonvulsant Activity of 3-(6-Substituted-benzothiazol-2-yl)-6-phenyl-[1,3]-xazinane-2-thiones. Arch Pharm, 335: 381‑388.
- Yang, Z., Wang, A., Chen, X., Gui, Q., Liu, J., Tan, Z. (2013). Synthesis of 2-Aryl Benzothiazoles via K2S2O8-Mediated Oxidative Condensation of Benzothiazoles with Benzylamines. Synlett, 24: 1549‑1554.
- Sadhasivam, G., Kulanthai, K., Natarajan, A. (2015). Synthesis and Anti-cancer Studies of 2, 6-disubstituted Benzothiazole Derivatives. Orient J Chem, 31: 819‑826.
- Sharma, A.K., Kim, J., Prior, J.T., Hawco, N.J., Rath, N. P., Kim, J. (2014). Small Bifunctional Chelators That Do Not Disaggregate Amyloid β Fibrils Exhibit Reduced Cellular Toxicity. Inorg Chem, 53: 11367‑11376.
- Lashkari, M., Maghsoodlou, M.T., Karima, M., Adrom, B., Fatahpour, M. (2016). Convenient Approach for the One-Pot, Three-Component Synthesis of 1-(Benzothiazolylamino)Methyl-2- Naphthol Using Citric Acid as a Green Catalyst. Acta Chem Iasi, 24: 212-221.
- Adrom, B., Maghsoodlou, M.T., Hazeri, N., Lashkari, M. (2015). Solvent-free synthesis of 1-(benzothiazolylamino)methyl-2-naphthols with maltose as green catalyst. Res Chem Intermed, 41: 7553‑7560.
- Shaabani, A., Rahmati, A., Farhangi, E. (2007). Water promoted one-pot synthesis of 2′-aminobenzothiazolomethyl naphthols and 5-(2′-aminobenzothiazolomethyl)-6-hydroxyquinolines. Tetrahedron Lett, 48: 7291‑7294.
- Kumar, A., Rao, M.S., Rao, V.K. (2010). Sodium Dodecyl Sulfate-assisted Synthesis of 1-(Benzothiazolylamino)methyl-2-naphthols in Water. Aust J Chem, 63: 1538-1540.
- Shaterian, H.R., Hosseinian, A.A. (2015). Brønsted acidic ionic liquid, [(CH2)3SO3HMIM][HSO4], as an efficient catalyst for synthesis of 1-(benzothiazolylamino)methyl-2-naphthols. Res Chem Intermed, 41: 793‑801.
- Maghsoodlou, M.T., Karima, M., Lashkari, M., Adrom, B., Aboonajmi, J. (2017). A green protocol for one-pot three-component synthesis of 1-(benzothiazolylamino) methyl-2-naphthol catalyzed by oxalic acid. J Iran Chem, 14: 329‑335.
- Bahammou, I., Esaady, A., Boukhris, S., Ghailane, R., Habbadi, N., Hassikou, A., Souizi, A. (2016). Direct use of mineral fertilizers MAP, DAP, and TSP as heterogeneous catalysts in organic reactions. Mediterr J Chem, 5: 615-623.
- Sibous, S., Ghailane, T., Houda, S., Ghailane, R., Boukhris, S., Souizi, A. (2017). Green and efficient method for the synthesis of 1,5-benzodiazipines using phosphate fertilizers as catalysts under free solvent. Mediterr J Chem, 6: 53-59.
- Sibous, S., Boukhris, S., Ghailane, R., Habbadi, N., Hassikou, A., Souizi, A. (2017). Easy synthesis of 3,4-dihydropyrimidin -2-(1H)-ones using phosphate fertilizers MAP, DAP and TSP as efficient catalysts. J Turk Chem Soc Sect Chem, 4: 477-488.
- Venkatesan, K., Pujari, S.S., Lahoti, R.J., Srinivasan, K.V. (2008). An efficient synthesis of 1,8-dioxo-octahydro-xanthene derivatives promoted by a room temperature ionic liquid at ambient conditions under ultrasound irradiation. Ultrason Sonochem, 15: 548‑553.
- Hosseinian, A., Shaterian, H. R. (2012). NaHSO4.H2O Catalyzed Multicomponent Synthesis of 1-(Benzothiazolylamino) Methyl-2-Naphthols Under Solvent-Free Conditions. Phosphorus Sulfur Silicon Relat Elem, 187: 1056‑1063.
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