Thiazole formation through a modified Gewald reaction

Scholarly Works

• Zhang, M.; Chen, Y.; Yan, X.; Zhang, Y.; Ma, X. Synthesis of hydroxy-thiazoline substituted pyridine derivatives via [3 + 2] annulation of 1,4-dithiane-2,5-diol with cyanopyridine. Organic & biomolecular chemistry 2024. doi:10.1039/d4ob01388c
• Zeng, Q.; Hui, Y.; Wang, Y.; Wen, K.; Huang, J.; Zhang, Y.; Wang, Y.; Zhang, S. An efficient synthesis of 2-aminothiophenes via the Gewald reaction catalyzed by enzymes in ionic liquids. Journal of Molecular Structure 2023, 1294, 136511. doi:10.1016/j.molstruc.2023.136511
• Prieschl, M.; Sedelmeier, J.; Püntener, K.; Hildbrand, S.; Williams, J. D.; Kappe, C. O. Rediscovering Cyanogen Gas for Organic Synthesis: Formation of 2-Cyanothiazole Derivatives. The Journal of organic chemistry 2023, 88, 9594–9598. doi:10.1021/acs.joc.3c01110
• Srour, A. M.; Fahmy, H. H.; Khater, M. A.; Zarie, E. S.; Mohamed, S. S.; Abdelhameed, M. F. Synthesis, anti-inflammatory properties, molecular modelling and potential COX-2, TNF-α, PGE2 and IL1β inhibitors of pyrazole-based scaffolds. Journal of Molecular Structure 2022, 1266, 133499. doi:10.1016/j.molstruc.2022.133499
• Sahil; Kaur, K.; Jaitak, V. Thiazole and Related Heterocyclic Systems as Anticancer Agents: A Review on Synthetic Strategies, Mechanisms of Action and SAR Studies. Current medicinal chemistry 2022, 29, 4958–5009. doi:10.2174/0929867329666220318100019
• Duc, D. X.; Chung, N. T. Recent Development in the Synthesis of Thiazoles. Current organic synthesis 2022, 19, 702–730. doi:10.2174/1570179419666220216122637
• De, S. K. doi:10.1002/9783527828166.ch7
• Röder, L.; Nicholls, A. J.; Baxendale, I. R. Flow Hydrodediazoniation of Aromatic Heterocycles. Molecules (Basel, Switzerland) 2019, 24, 1996. doi:10.3390/molecules24101996
• Wilk, M.; Trzepizur, D.; Koszelewski, D.; Brodzka, A.; Ostaszewski, R. Synthesis of (E)-α,β-unsaturated carboxylic esters derivatives from cyanoacetic acid via promiscuous enzyme-promoted cascade esterification/Knoevenagel reaction. Bioorganic chemistry 2019, 93, 102816. doi:10.1016/j.bioorg.2019.02.041
• Nayak, S.; Gaonkar, S. L. A Review on Recent Synthetic Strategies and Pharmacological Importance of 1,3-Thiazole Derivatives. Mini reviews in medicinal chemistry 2019, 19, 215–238. doi:10.2174/1389557518666180816112151
• Fadda, A. A.; Tawfik, E. H.; Selim, Y. A. Synthesis and Biological Evaluation of Some New Thiophene, Thiazole, Dithiolane Derivatives and Related Compounds. Polycyclic Aromatic Compounds 2018, 40, 1445–1458. doi:10.1080/10406638.2018.1555174
• Isadora, S. L.; da Cruz Rayssa, M. D.; da Cruz Ryldene Marques, D.; de Araújo Rodrigo, S. A.; Francisco, J. B. M.-J. 1,4-Dithiane-2,5-diol: A Versatile Synthon for the Synthesis of Sulfur-containing Heterocycles. Current Organic Synthesis 2018, 15, 1026–1042. doi:10.2174/1570179415666180821154551
• Zamberlan, F.; Fantinati, A.; Trapella, C. 1,4‐Dithiane‐2,5‐diol: An Attractive Platform for the Synthesis of Sulfur Containing Functionalized Heterocycles. European Journal of Organic Chemistry 2018, 2018, 3248–3264. doi:10.1002/ejoc.201701785
• Hu, C.; Hong, G.; Qian, X.; Kim, K. R.; Zhu, X.; Wang, L. AlCl3 catalyzed coupling of N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon–nitrogen bond cleavage. Organic & biomolecular chemistry 2017, 15, 4984–4991. doi:10.1039/c7ob01025g
• Reddy, G. V. S.; Chandrappa, M.; Gowda, V. N. P.; Rahaman, F.; Kumar, S. G.; Murthy, B. N.; Pullela, P. K. Efficient bulk scale synthesis of popular pesticide synthon: tetrachlorothiophene. Catalysis, Structure & Reactivity 2017, 3, 138–145. doi:10.1080/2055074x.2017.1327472
• Kumara, C. S. P.; Gowda, G. B.; Kumar, K. V.; Ramesh, N.; Sadashiva, M. P.; Junjappa, H. Base catalyzed reaction of 1,4-dithiane-2,5-diol with α-oxoketene dithioacetals: a new general method for the synthesis of 2-methylthio-3-aroyl/heteroaroyl thiophenes. Tetrahedron Letters 2016, 57, 4302–4305. doi:10.1016/j.tetlet.2016.08.033
• Du, J.; Tao, M.; Zhang, W. Fiber-Supported Acid–Base Bifunctional Catalysts for Efficient Nucleophilic Addition in Water. ACS Sustainable Chemistry & Engineering 2016, 4, 4296–4304. doi:10.1021/acssuschemeng.6b00785
• Wu, Y.-J. Five-Membered Ring Systems: With N and S Atom. Progress in Heterocyclic Chemistry 2016, 28, 317–339. doi:10.1016/b978-0-08-100755-6.00009-0
• Mallia, C. J.; Englert, L.; Walter, G. C.; Baxendale, I. R. Thiazole Formation Through a Modified Gewald Reaction. ChemInform 2015, 46. doi:10.1002/chin.201533173
• Mallia, C. J.; Englert, L.; Walter, G. C.; Baxendale, I. R. Ethyl 2-hydroxy-2-phenyl-2-(thiazol-2-yl)acetate. Molbank 2015, 2015, M857. doi:10.3390/m857

Explore citations to this article at