New Method of 2-Substituted Benzothiazole Synthesis from 2-Aminothiophenol Derivatives and Acetophenone
Main Article Content
Abstract
Benzothiazole is one of the compounds with many interesting biological activities. The synthetic methods previously studied have been carried out under complex conditions such as under strong acidic environment, high temperature or expensive catalysts and undergo many reaction steps. In this study, we report a new method of synthesizing benzothiazole in a reaction step under no solvent, no metal catalysts, using low-cost starting materials. The ability to participate in the reaction of various 2-aminothiophenol derivatives has been investigated and the product has obtained a fairly to excellent performance. We have successfully synthesized seven derivatives of benzothiazole with good yield under mild conditions.
Keywords
1,3 benzothiazoles, 2-aminothiophenol, sulfur, acetophenone
Article Details
References
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[2] C. Lamberth, H. Walter, F. K. Murphy, L. Quaranta, R. Beaudegnies, S. Trah, A. Jeanguenata and F. Cederbaum. Synthesis and Antiviral Activity of Novel α-Aminophosphorus Containing Benzofuran Moiety . Phosphorus, Sulfur Silicon Relat. Elem., 190, (2015), 1225.
[3] D. J. Parker, H. A. Jones, S. Petcher, L. Cervini, J. M. Griffin, R. Akhtar and T. Hasell. Low cost and renewable sulfur-polymers by inverse vulcanisation, and their potential for mercury capture J. Mater. Chem. A, Q8 (2017). https://doi.org/10.1039/C6TA09862B;
[4] M. J. H. Worthington, R. L. Kucer and J. M. Chalker. Green chemistry and polymers made from sulfur. Green Chem., 19, (2017), 2748.
[5] T. B. Nguyen. Recent advances in organic reactions involving elemental sulfur. Adv. Synth. Catal., 359, (2017), 1066.
[6] T. B. Nguyen. Elemental Sulfur and Molecular Iodine as Efficient Tools for Carbon‐Nitrogen Bond Formation through Redox Reactions. Asian J. Org. Chem., 6, (2017), 477. https://doi.org/10.1002/ajoc.201700011.
[7] D. L. Priebbenow and C. Bolm. Recent advances in the Willgerodt–Kindler reaction. Chem. Soc.Rev., 42, (2013), 7870.
[8] Z. Puterova, A. Krutosikova and D. Vegh. Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes. ARKIVOC, (2010), 209.
[9] F. Asinger. Optisch aktives 2-Phenyl-3,4-dimethylmorpholin. Angew. Chem., 68, (1956), 413.
[10] F. Asinger. Prüfung und Verarbeitung von Arzneidrogen. Angew. Chem., 68, (1956), 377.
[11] I. Schlemminger, H. Janknecht, W. Maison, W. Saak and J. Martens. Synthesis of the first enantiomerically pure 3-thiazolines via Asinger reaction. Tetrahedron Lett., 41, (2000), 7289.
[12] T. B. Nguyen, L. Ermolenko and A. Al-Mourabit. Nitro-Methyl Redox Coupling: Efficient Approach to 2-Hetarylbenzothiazoles from 2-Halonitroarene, Methylhetarene, and Elemental Sulfur. Org. Lett., 15, (2013), 4218.
[13] T. B. Nguyen, P. Retailleau, L. Ermolenko and A. Al-Mourabit. Elemental Sulfur Disproportionation in the Redox Condensation Reaction between o‐Halonitrobenzenes and Benzylamines. Angew. Chem., Int. Ed., 53, (2014), 13808.
[14] T. B. Nguyen, K. Pasturaud, L. Ermolenko and A. Al-Mourabit. Concise Access to 2-Aroylbenzothiazoles by Redox Condensation Reaction between oHalonitrobenzenes, Acetophenones, and Elemental Sulfur. Org. Lett., 17, (2015), 2562.
[15] T. Guntreddi, R. Vanjari and K. N. Singh. Elemental Sulfur Mediated Decarboxylative Redox Cyclization Reaction of o-Chloronitroarenes and Arylacetic Acids. Org. Lett., 17, (2015), 976.
[16] Y. Tong, Q. Pan, Z. Jiang, D. Miao, X. Shi and S. Han. A simple approach to benzothiazoles from 2-chloronitrobenzene, elemental sulfur, and aliphatic amine under solvent-free and catalyst-free conditions. Tetrahedron Lett., 55, (2014), 5499.
[17] T. B. Nguyen, P. Retailleau. Elemental sulfur-promoted oxidative rearranging coupling between o-aminophenols and ketones: a synthesis of 2-alkyl benzoxazoles under mild conditions. Organic Letter. 19, (2017), 3887.
[18] Gao, X.; Liu, J.; Zuo, X.; Feng, X.; Gao, Y. Recent Advances in Synthesis of Benzothiazole Compounds Related to Green Chemistry. Molecules, 25, (2020), 1675.
[19] Thanh Binh Nguyen, Karine Pasturaud, Ludmila Ermolenko, and Ali Al-Mourabit. Concise Access to 2-Aroylbenzothiazoles by Redox Condensation Reaction between oHalonitrobenzenes, Acetophenones, and Elemental Sulfur. Organic Letter 17, (2015), 2562.