New Method of 2-Arylbenzoxazole Synthesis from 2-Aminophenol Derivatives and Benzaldehyde Using Sulfur as an Oxidant
Main Article Content
Abstract
In previous studies, the synthesis of 2-arylbenzoxazole derivatives required strongly acidic conditions, prolonged heating at high temperatures and significant amounts of expensive/toxic transition metal catalysts. A major drawback of using oxygen as an oxidant is the risk of explosion of flammable organic substrates. Moreover, due to its gaseous state, exact stoichiometric control of oxygen amounts used in the reaction is not readily possible. Therefore, new methods of mellow conditions with eco-friendly agents is targeted by our team. In this study, sulfur (S8) is found as an effective oxidizer in the oxidation reaction condensation between 2-aminophenols with benzaldehydes to obtain different 2-arylbenzoxazole. In the presence of Na2S as catalysts and DMSO as an additive the reactions give good yield in only one step at the ambient temperature.
Keywords
Sulfur, Na2S, 2-arylbenzoxazole, oxidative condensation
Article Details
References
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[26] Nguyen, T. B., Retailleau, P. Elemental Sulfur as Reaction Medium for the Synthesis of Fused Nitrogen Heterocycles by Oxidative Coupling between Cycloalkanones and Nitrogen Nucleophiles. Adv. Synth. Catal. 359, (2017), 3843.
[27] Nguyen, T. B., Nguyen, L. A., Retailleau P. Strategy for Contiguous Tetramination of Cyclohexanones with o-Phenylenediamines with Elemental Sulfur and DMSO. Org. Lett. 21, (2019), 6570.
[28] Nguyen, T. B., Recent Advances in the Synthesis of Heterocycles via Reactions Involving Elemental Sulfur. Advance Synthesis & Catalysis (2020). https://doi.org/10.1002/adsc.202000535
[2] Ram, V. J Sethi, S. Nath, M. Pratap, R. Five-Membered Heterocycles. In The Chemistry of Heterocycles Nomenclature and Chemistry of Three-to-Five Membered Heterocycles; Elsevier, (2019), 149-478.
[3] Kangani, C. O. Kelley, D. E. Day, B. W. One pot direct synthesis of oxazolines, benzoxazoles, and oxadiazoles from carboxylic acids using the Deoxo-Fluor reagent. Tetrahedron Lett., 47, (2006), 6497-6499.
[4] Wang, Y. Sarris, K. Sauer, D. R. Djuric, S. W. A. A simple and efficient one step synthesis of benzoxazoles and benzimidazoles from carboxylic acids. Tetrahedron Lett., 47, (2006), 4823-4826.
[5] Tan, H. Pan, C. Xu, Y. Wang, H. Pan, Y. Synthesis of benzoxazoles by the copper triflate catalysed reaction of nitriles and o-aminophenols. J. Chem. Res., 36, (2012), 370-373.
[6] Kumar, D. Rudrawar, S. Chakraborti, A. K. One-pot synthesis of 2-substituted benzoxazoles directly from carboxylic acids. Australian J. Chem., 61, (2008), 881-887.
[7] Yu, J. Xu, J. Lu, M. Copper‐catalyzed highly efficient aerobic oxidative synthesis of benzimidazoles, benzoxazoles and benzothiazoles from aromatic alcohols under solvent‐free conditions in open air at room temperature. App. Organomet. Chem. 27, (2013), 606-610.
[8] Shi, Xinkang Guo, Junmei Liu, Jianping Ye, Mingde Xu, Q. Unexpectedly Simple Synthesis of Benzazoles by tBuONa‐Catalyzed Direct Aerobic Oxidative Cyclocondensation of o‐Thio/Hydroxy/Aminoanilines with Alcohols under Air. Chem. Eur. J., 21, (2015), 9988-9993.
[9] Nguyen, T. B. Ermolenko, L. Dean, W. A. Almourabit, A. Benzazoles from Aliphatic Amines and o-Amino/Mercaptan/Hydroxyanilines: Elemental Sulfur as a Highly Efficient and Traceless Oxidizing Agent. Org. Lett., 14, (2012), 5948-5951.
[10] Endo, Y. Bäckvall, J.-E. Biomimetic Oxidative Coupling of Benzylamines and 2‐Aminophenols: Synthesis of Benzoxazoles. Chem. Eur. J., 18, (2012), 13609-13613.
[11] Nguyen, T. B. Retailleau, P. Elemental Sulfur-Promoted Oxidative Rearranging Coupling between o-Aminophenols and Ketones: A Synthesis of 2-Alkyl benzoxazoles under Mild Conditions. Org. Lett., 19, (2017), 3887-3891.
[12] Cho, Y. Lee, C; Ha, D. Cheon, C. Cyanide as a Powerful Catalyst for Facile Preparation of 2‐Substituted Benzoxazoles via Aerobic Oxidation. Adv. Synth. Catal., 354, (2012), 2992-2996.
[13] Chen, G. Shen, H.; Zhang, L. Li, H. Lan, R. Chen, B. Li, J. Hu, Q., One-pot Synthesis of 2-Substituted Benzoxazoles Promoted by Copper Acetate Monohydrate. Lett. Org. Chem. 11, (2014), 180-187.
[14] Chang, W. Sun, Y. Huang, Y. One‐pot green synthesis of benzoxazole derivatives through molecular sieve‐catalyzed oxidative cyclization reaction. Heteroatom Chem., 28, (2017), 21360.
[15] Karimian, A. Mohammadzadeh K., Roya Kargar Beidokhti, H. Magnetic Co‐doped NiFe2O4 Nanocomposite: A Heterogeneous and Recyclable Catalyst for the One‐Pot Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles under Solvent‐Free Conditions. J. Chinese Chem. Soc., 64, (2017), 1316-1325.
[16] Gu, L. Jin, C. Guo, J. Zhang, L. Wang, W. A novel strategy for the construction of substituted benzoxazoles via a tandem oxidative process. Chem. Commun., 49, (2013), 10968-10970.
[17] Nguyen, T. B. Nguyen, L. P. A. Nguyen, T. T. T. Sulfur‐Catalyzed Oxidative Coupling of Dibenzyl Disulfides with Amines: Access to Thioamides and Aza Heterocycles. Adv. Synth. Catal., 361, (2019), 1787-1791.
[18] Tang, L. Guo, X. Yang, Y. Zha, Z. Wang, Z. Gold nanoparticles supported on titanium dioxide: an efficient catalyst for highly selective synthesis of benzoxazoles and benzimidazoles. Chem. Commun., 50, (2014), 6145-6148.
[19] Khalafi-Nezhad, A. Panahi, F. Ruthenium-Catalyzed Synthesis of Benzoxazoles Using Acceptorless Dehydrogenative Coupling Reaction of Primary Alcohols with 2-Aminophenol under Heterogeneous Conditions. ACS Catalysis., 4, (2014), 1686-1692.
[20] He, Jian Lin, Fu Yang, Xufang Wang, Di Tan, Xiaohua Zhang, S. Sustainable synthesis of 2-arylbenzoxazoles over a cobalt-based nanocomposite catalyst. Org Proc. Res. Dev., 20, (2016), 1093-1096.
[21] Fan, X. He, Y. Wang, Y. Zhang, X. Wang, An Efficient Synthesis of 2‐Substituted Benzoxazoles via RuCl3·3H2O Catalyzed Tandem Reactions in Ionic Liquid. J. Chinese J. Chem., 29, (2011), 773-777.
[22] Nguyen, T. B., Recent Advances in Organic Reactions Involving Elemental Sulfur. Adv. Synth. Catal. 359, (2017), 1106.
[23] Nguyen, T. B., Asian J. Org. Chem., 6, (2017), 477.
[24] Nguyen, T. B., Retailleau, P. Redox-Neutral Access to Sultams from 2-Nitrochalcones and Sulfur with Complete Atom Economy. Org. Lett., 19, (2017), 3879.
[25] Nguyen, L. A., Ngo, Q. A., Retalleau, P. Nguyen, T., Elemental sulfur as a polyvalent reagent in redox condensation with o-chloronitrobenzenes and benzaldehydes: three-component access to 2-arylbenzothiazoles. Green Chem. 19, (2017), 4289.
[26] Nguyen, T. B., Retailleau, P. Elemental Sulfur as Reaction Medium for the Synthesis of Fused Nitrogen Heterocycles by Oxidative Coupling between Cycloalkanones and Nitrogen Nucleophiles. Adv. Synth. Catal. 359, (2017), 3843.
[27] Nguyen, T. B., Nguyen, L. A., Retailleau P. Strategy for Contiguous Tetramination of Cyclohexanones with o-Phenylenediamines with Elemental Sulfur and DMSO. Org. Lett. 21, (2019), 6570.
[28] Nguyen, T. B., Recent Advances in the Synthesis of Heterocycles via Reactions Involving Elemental Sulfur. Advance Synthesis & Catalysis (2020). https://doi.org/10.1002/adsc.202000535