|
|
氨基噻唑合成研究进展
|
Abstract:
噻唑类化合物具有广泛的生物活性，其中，氨基噻唑作为重要结构单元在药物和药物化学领域中广泛存在。然而原有的Hantzsch合成法存在许多弊端，研究者对其进行了一系列改进，并发现了一些新的合成方法。本文主要从非均相纳米催化合成氨基噻唑，光催化合成氨基噻唑，未使用催化剂合成氨基噻唑，使用绿色溶剂合成氨基噻唑，熔融法合成氨基噻唑，硫氰酸根参与的氨基噻唑合成，其他等方面阐述近几年氨基噻唑的合成研究进展。
Thiazole compounds have a wide range of biological activities. Among of them, 2-aminothiazoles are one of the most important classes of heterocycles in the field of pharmaceutical and medicinal chemistry such as antifungal, insecticidal, radioprotective, bactericidal, antiviral, and anesthetic ac-tivities. The original Hantzsch synthesis has many disadvantages, and researchers have made a se-ries of improvements. This article mainly describes the progress of the synthesis of aminothiazole in recent years.
| [1] | Gouda, M.A., Berghot, M.A., Baz, E.A., et al. (2012) Synthesis, Antitumor and Antioxidant Evaluation of Some New Thiazole and Thiophene Derivatives Incorporated Coumarin Moiety. Medicinal Chemistry Research, 21, 1062-1070.
https://doi.org/10.1007/s00044-011-9610-8 |
| [2] | Simmons, M.S. (1996) The Role of Catalysts in Environmentally Benign Synthesis of Chemicals. In: Anastas, P.T. and Williamson, T.C., Eds., Green Chemistry, ACS Symposium Se-ries Volume 626, American Chemical Society, Washington DC, 116-130. |
| [3] | Abdolmohammadi, S. (2013) Simple Route to Indeno[1,2-b]quinoline Derivatives via a Coupling Reaction Catalyzed by TiO2 Nanoparticles. Chinese Chemi-cal Letters, 24, 318-320. |
| [4] | Safari, J., Abedi-Jazini, Z., Zarnegar, Z., et al. (2015) TiO2 Nanoparticles Supported on the Fe3O4@SiO2 Nanocomposites: A Novel Magnetic Nanocatalyst for the Synthesis of 2-Aminothiazoles. Journal of Nanoparticle Research, 17, 495. https://doi.org/10.1007/s11051-015-3298-5 |
| [5] | Safari, J., Abedi-Jazini, Z., Zarnegar, Z., et al. (2016) Nanochitosan: A Biopolymer Catalytic System for the Synthesis of 2-Aminothiazoles. Cataly-sis Communications, 77, 108-112. https://doi.org/10.1016/j.catcom.2016.01.007 |
| [6] | Safari, J. and Sadeghi, M. (2017) Nanostarch: A Novel and Green Catalyst for Synthesis of 2-Aminothiazoles. Monatshefte für Chemie Chemical Monthly, 148, 745-749. https://doi.org/10.1007/s00706-016-1805-8 |
| [7] | Sadeghi, M., Safari, J. and Zarnegar, Z. (2016) Synthesis of 2-Aminothiazoles from Methylcarbonyl Compounds Using a Fe3O4 Nanoparticle-N-Halo Reagent Catalytic System. RSC Advances, 6, 64749-64755.
https://doi.org/10.1039/C6RA11175K |
| [8] | Sharma, A., Gudala, S., Ambati, S.R., et al. (2018) On-Water NiFe2O4 Nanoparticle-Catalyzed One-Pot Synthesis of Biofunctionalized Pyrimidine-Thiazole Derivatives: In Silico Binding Af-finity and in Vitro Anticancer Activity Studies. Chemistry Select, 3, 11012-11019. https://doi.org/10.1002/slct.201801414 |
| [9] | Zarnegar, Z., Shokrani, Z. and Safari, J. (2019) Asparagine Function-alized Al2O3 Nanoparticle as a Superior Heterogeneous Organocatalyst in the Synthesis of 2-Aminothiazoles. Journal of Molecular Structure, 1185, 143-152.
https://doi.org/10.1016/j.molstruc.2019.02.080 |
| [10] | Roslan, I.I., Ng, K.H., Gondal, M.A., et al. (2018) Visible Light-Mediated Coupling of Thioureas and 1,3-Dicarbonyls: Towards a Leaving Group-Free Synthesis of Aminothia-zoles. Advanced Synthesis & Catalysis, 360, 1584-1589.
https://doi.org/10.1002/adsc.201701565 |
| [11] | Ghodse, S.M. and Telvekar, V.N. (2015) Synthesis of 2-Aminothiazole Derivatives from Easily Available Thiourea and Alkyl/Aryl Ketones Using Aqueous NaICl2. Tetrahe-dron Letters, 56, 472-474.
https://doi.org/10.1016/j.tetlet.2014.11.140 |
| [12] | Abedi-Jazini, Z., Safari, J., Zarnegar, Z., et al. (2018) A Simple and Efficient Method for the Synthesis of 2-Amino- thiazoles under Mild Conditions. Polycyclic Aromatic Compounds, 38, 231-235.
https://doi.org/10.1080/10406638.2016.1200104 |
| [13] | Zarnegar, Z., Sadeghi, M., Alizadeh, R., et al. (2018) HX-DMSO: A Novel Liquid Halogenating System for Synthesis of 2-Aminothiazoles via Csp3H Bond Functionaliza-tion. Journal of Molecular Liquids, 255, 76-79.
https://doi.org/10.1016/j.molliq.2018.01.119 |
| [14] | Sun, J., Ge, H., Zhen, X., et al. (2018) TBHP/AIBN-Mediated Synthesis of 2-Amino-Thioazoles from Active Methylene Ketones and Thiourea under Metal-Free Conditions. Tetrahe-dron, 74, 2107-2114.
https://doi.org/10.1016/j.tet.2018.02.064 |
| [15] | Wagare, D.S., Netankar, P.D., Shaikh, M., et al. (2017) Highly Effi-cient Microwave-Assisted One-Pot Synthesis of 4-aryl-2-aminothiazoles in Aqueous Medium. Environmental Chemistry Letters, 15, 475-479.
https://doi.org/10.1007/s10311-017-0619-1 |
| [16] | Zhao, J., Xu, J., Chen, J., et al. (2015) Potassium Iodide and Ammonium Nitrate Catalyzed Aerobic Oxidative Cyclization of Ketones with Thioureas in Ionic Liquid: An Access to 2-Aminothiazoles. Tetrahedron, 71, 539-543.
https://doi.org/10.1016/j.tet.2014.12.044 |
| [17] | Azizi, N., Rahimi, Z. and Alipour, M. (2015) Deep Eutectic Sol-vent-Assisted One-Pot Synthesis of 2-Aminothiazole and 2-Aminoxazole Derivatives. Comptes Rendus Chimie, 18, 626-629. https://doi.org/10.1016/j.crci.2014.10.001 |
| [18] | Prevost, J.R.C., Kozlova, A., Saadi, B.E., et al. (2018) Convenient One-Pot Formation of Highly Functionalized 5-Bromo-2-aminothiazoles, Potential Endocannabinoid Hydro-lase MAGL Inhibitors. Tetrahedron Letters, 59, 4315-4319.
https://doi.org/10.1016/j.tetlet.2018.10.055 |
| [19] | Facchinetti, V., Avellar, M.M., Nery, A.C.S., et al. (2016) An Eco-Friendly, Hantzsch-Based, Solvent-Free Approach to 2-Aminothiazoles and 2-Aminoselenazoles. Synthesis, 48, 437-440. https://doi.org/10.1055/s-0035-1560534 |
| [20] | Zali-Boeini, H. and Mansouri, S.G. (2016) One-Step Three-Component and Solvent-Free Synthesis of Thiazoles from Tertiary Thioamides. Journal of the Iranian Chemical Society, 13, 1571-1577.
https://doi.org/10.1007/s13738-016-0873-3 |
| [21] | Ghorbani-Vaghei, R., Alavinia, S., Merati, Z., et al. (2018) MNPs@ SiO2-Pr-AP: A New Catalyst for the Synthesis of 2-Amino-4-aryl Thiazole Derivatives. Applied Organometal-lic Chemistry, 32, e4127. https://doi.org/10.1002/aoc.4127 |
| [22] | Meshram, H.M., Thakur, P.B., Babu, B.M., et al. (2012) Convenient and Simple Synthesis of 2-Aminothiazoles by the Reaction of α-Halo Ketone Carbonyls with Ammo-nium Thiocyanate in the Presence of N-Methylimidazole. Tetrahedron Letters, 53, 5265-5269. https://doi.org/10.1016/j.tetlet.2012.07.080 |
| [23] | Samimi, H.A. and Mohammadi, S. (2014) New One-Pot Approach to Regio-Synthesis of Substituted 2-Aminothiazoles from the Corresponding Keto-Aziridines. Journal of the Iranian Chemical Society, 11, 69-73.
https://doi.org/10.1007/s13738-013-0276-7 |
| [24] | Zhang, G., Chen, B., Guo, X., et al. (2015) Iron (II)-Promoted Synthesis of 2-Aminothiazoles via C-N Bond Formation from Vinyl Azides and Potassium Thiocyanate. Advanced Syn-thesis & Catalysis, 357, 1065-1069.
https://doi.org/10.1002/adsc.201400856 |
| [25] | Tang, X., Zhu, Z., Qi, C., et al. (2016) Copper-Catalyzed Coupling of Oxime Acetates with Isothiocyanates: A Strategy for 2-Aminothiazoles. Organic Letters, 18, 180-183. https://doi.org/10.1021/acs.orglett.5b03188 |
| [26] | Richter, F., Seifert, J., Korb, M., et al. (2018) Real Multicompo-nent Reactions: Synthesis of Highly Substituted 2-Aminothiazoles. European Journal of Organic Chemistry, 2018, 4673-4682. https://doi.org/10.1002/ejoc.201800701 |
| [27] | Zhu, Y., Chen, W., Zhao, D., et al. (2019) One-Pot Three-Component Strategy for Polysubstituted 2-Aminothiazoles via Ring Opening of α-Nitro Epoxides. Synthesis, 51, 2023-2029. https://doi.org/10.1055/s-0037-1612101 |
| [28] | Chen, B., Guo, S., Guo, X., et al. (2015) Selective Ac-cess to 4-Substituted 2-Aminothiazoles and 4-Substituted 5-Thiocyano-2-aminothiazoles from Vinyl Azides and Potas-sium Thiocyanate Switched by Palladium and Iron Catalysts. Organic Letters, 17, 4698-4701. https://doi.org/10.1021/acs.orglett.5b02152 |
| [29] | Wang, Y., Zhao, F., Chi, Y., et al. (2014) Substituent-Controlled Selective Synthesis of N-acyl 2-Aminothiazoles by Intramolecular Zwitterion-Mediated C-N Bond Cleavage. The Journal of Organic Chemistry, 79, 11146-11154.
https://doi.org/10.1021/jo502123k |
| [30] | Guo, S., Zhao, D., Zhu, Y., et al. (2017) One-Pot Three-Component Pro-tocol for the Synthesis of Substituted 2-Aminothiazoles. Synthetic Communications, 47, 1758-1764. https://doi.org/10.1080/00397911.2017.1350275 |
| [31] | Ma, C., Miao, Y., Zhao, M., et al. (2018) Synthesis of 2-Aminothiazoles from Styrene Derivatives Mediated by 1,3-Dibromo-5,5-dimethylhydrantoin (DBH). Tetrahedron, 74, 3602-3607. https://doi.org/10.1016/j.tet.2018.05.021 |
