Facile and convenient synthesis of 2,4-disubstituted and 2,3,4-trisubstituted 1,3-thiazoles

References

• Little TL, Webber SE. A simple and practical synthesis of 2-aminoimidazoles. J Org Chem. 1994;59:7299–7305. doi: 10.1021/jo00103a021
   Web of Science ®Google Scholar
• Bramley SE, Dupplin V, Goberdhan DGC. The Hantzsch thiazole synthesis under acidic conditions: change of regioselectivity. J. Chem. Soc. Perkin. Trans. 1987;1:639–643. doi: 10.1039/p19870000639
   Google Scholar
• Shahvelayati AS, Yavari I, Delbari AS. Formation of thiazol-2(3H)imines by reaction of α-amino acids, aroylisothiocyanates, and α-bromoketones in an ionic liquid. Chin Chem Lett. 2014;25:119–122. doi: 10.1016/j.cclet.2013.11.009
   Web of Science ®Google Scholar
• Lin J-R, Li D-D, Wang A-R, et al. Design and synthesis of thiazole derivatives as potent Fab H inhibitors with antibacterial activity. Eur J Med Chem. 2014;75:438–447. doi: 10.1016/j.ejmech.2013.11.020
   PubMed Web of Science ®Google Scholar
• Thomae D, Perspicace E, Xu Z, et al. One-pot synthesis of new 2,4,5-trisubstituted 1,3-thiazoles and 1,3-selenazoles. Tetrahedron. 2009;65:2982–2988. doi: 10.1016/j.tet.2009.01.104
   Web of Science ®Google Scholar
• Dunst C, Knochel P. Regioselective functionalization of the thiazole scaffold using TMPMgCl.LiCl and TMP2Zn.2MgCl2.2LiCl. J Org Chem. 2011;76:6972–6978. doi: 10.1021/jo201250n
   PubMed Web of Science ®Google Scholar
• Li Z, Ma Li, Tang C, Xu J, Wu X, Yao H. Palladium(II)-catalyzed oxidative Heck coupling of thiazole-4-carboxylates. Tetrahedron Lett. 2011;52:5643–5647. doi: 10.1016/j.tetlet.2011.08.088
   Web of Science ®Google Scholar
• Peteira R, Gaudon C, Iglesias B, Germain P, Gronemeyer J, Delera AR. Synthesis of the PPARβ/δ-selective agonist GW501516 and C4-thiazole-substituted analogs. Bioorg Med Chem Lett. 2006;16:49–54. doi: 10.1016/j.bmcl.2005.09.060
   PubMed Web of Science ®Google Scholar
• Kim DK, Choi JH, An YJ, Lee HS. Synthesis and biological evaluation of 5-(pyridin-2-yl)thiazoles as transforming growth factor-beta type1 receptor kinase inhibitors. Bioorg Med Chem Lett. 2008;18:2122–2127. doi: 10.1016/j.bmcl.2008.01.084
   PubMed Web of Science ®Google Scholar
• Kim SK, Kim J-H, Park YC, Kim JW, Yum EK. Synthesis of trisubstituted thiazoles by ligand-free palladium-catalyzed direct 5-arylation of 2,4-disubstituted thiazoles under conventional and microwave-assisted heating. Tetrahedron. 2013;69:10990–10995. doi: 10.1016/j.tet.2013.10.053
   Web of Science ®Google Scholar
• Yadav JS, Reddy BV, Rav YG, Narsaiah AV. First example of the coupling of α-diazoketones with thiourea: a novel route for the synthesis of 2-amino-thiazoles. Tetrahedron Lett. 2008;49:2381–2383. doi: 10.1016/j.tetlet.2008.02.068
   Web of Science ®Google Scholar
• Potewar TM, Ingale SA, Srinivasan KV. Efficient synthesis of 2,4-disubstituted thiazoles using ionic liquid under ambient conditions: a practical approach towards the synthesis of fanetizole. Tetrahedron. 2007;63:11066–11069. doi: 10.1016/j.tet.2007.08.036
   Web of Science ®Google Scholar
• Prakash R, Kumar A, Aggarwal R, Prakash O, Singh SP. α,α-Dibromoketones: A superior alternative to α-bromoketones in hantzsch thiazole synthesis. Synth. Commun. 2007;37:2501–2505. doi: 10.1080/00397910701462476
   Web of Science ®Google Scholar
• Narender M, Reddy MS, Sridhar R, Nageswar YVD, Rao KS. Aqueous phase synthesis of thiazoles and aminothiazoles in the presence of β-cyclodextrin. Tetrahedron Lett. 2005;46:5953–5955. doi: 10.1016/j.tetlet.2005.06.130
   Web of Science ®Google Scholar
• Kumar VP, Narender M, Sridhar R, Nageswar YVD, Rao KR. Synthesis of thiazoles and aminothiazoles from β-keto tosylates under supramolecular catalysis in the presence of β-cyclodextrin in water. Synth Commun. 2007;37:4331–4336. doi: 10.1080/00397910701575913
   Web of Science ®Google Scholar
• Miyamoto K, Nish Y, Ochiao M. Thiazole synthesis by cyclocondensation of 1-alkynyl(phenyl)-λ3-iodanes with thioureas and thioamides . Angew Chem Int Ed. 2005;44:6896–6899. doi: 10.1002/anie.200502438
   PubMed Web of Science ®Google Scholar
• Potewar TM, Ingale SA, Srinivasan KV. Catalyst-free efficient synthesis of 2-aminothiazoles in water at ambient temperature. Tetrahedron. 2008;64:5019–5022. doi: 10.1016/j.tet.2008.03.082
   Web of Science ®Google Scholar
• Zhu D, Chen J, Xiao H, Liu M, Ding J, Wu H. Efficient and expeditious Synthesis of di- and trisubstituted thiazoles in PEG under catalyst-free conditions. Synth Commun. 2009;39:2895–2906. doi: 10.1080/00397910802691874
   Web of Science ®Google Scholar
• Davyt D, Serra G. Thiazole and oxazole alkaloids: isolation and synthesis. Mar Drugs. 2010;8:2755–2780, and references therein. doi: 10.3390/md8112755
   PubMed Web of Science ®Google Scholar
• Kashyap SJ, Grag VK, Sharma PK, Kumar N, Dudhe R, Gupta JK. Thiazoles: having diverse biological activities. Med Chem Res. 2012;21:2123–2132, and references therein. doi: 10.1007/s00044-011-9685-2
   Web of Science ®Google Scholar
• Siddiqui N, Arshad MF, Ahsan W, Alam S. Thiazoles: a valuable insight into the recent advances and biological activities. Int J Pharm Sci Drug Res. 2009;1:136–143.
   Google Scholar
• Zagade AA, Senthiekumar GP. Thiazole: a valuable insight into recent advances, synthesis and biological activities. Pharma Chem. 2011;3:523–537.
   Google Scholar
• Zablotskaya A, Segal I, Geronikaki A, et al. Synthesis, physicochemical characterization, cytotoxicity, antimicrobial, anti-inflammatory and psychotropic activity of new N-[1,3-(benzo)thiazol-2-yl]-ω-[3,4-dihydroisoquinolin-2(1H)-yl]alkanamides. Eur J Med Chem. 2013;70:846–856, and references therein. doi: 10.1016/j.ejmech.2013.10.008
   PubMed Web of Science ®Google Scholar
• Bhattcharya S, Thomas M. Synthesis of a novel thiazole based dipeptide chemosensor for Cu(II) in water. Tetrahedron Lett. 2000;41:10313–10317. doi: 10.1016/S0040-4039(00)01853-0
   Web of Science ®Google Scholar
• Hassan AA, Mohamed SK, Mohamed NK, Elshaieb KMA, Abdel-Aziz AT, Abdel-Rahman MR. Synthesis and biological activity of 1,3-thiazolylidenehydrazinylidene ethylpyridiniumbromide monohydrate, 1,3- thiazolylidenehydraziniumbromide and 1,3-thiazolylidenehydrazine derivatives. J Adv Chem. 2015;11:3357–3366.
   Google Scholar
• D'hooghe M, De Kimpe N. Synthetic approaches towards 2-iminothiazolidines: an overview. Tetrahedron. 2006;62:513–535. doi: 10.1016/j.tet.2005.09.028
   Web of Science ®Google Scholar
• Werbel LM, Degnane MB, Harger GF, Capps DB, Islip PJ, Closier MD. 1-Alkyl-3-(3-alkyl-5-nitro-4-thiazolin-2-ylidene)ureas and related compounds as schistosomicides. J Med Chem. 1972;15:955–963. doi: 10.1021/jm00279a020
   PubMed Web of Science ®Google Scholar
• Zhou G-B, Guan Y-Q, Shen C, et al. A novel and convenient synthesis of thiazol- 2(3H)-imine-linked glycoconjugates. Synthesis. 2008;13:1994–1996. doi: 10.1055/s-2008-1067121
   Web of Science ®Google Scholar
• De Kimpe N, Boelens M, Declercq JP. A novel synthesis of 2-Imino-4-thiazolines via α-bromoketimines. Tetrahedron. 1993;49:3411–3424. doi: 10.1016/S0040-4020(01)90168-1
   Web of Science ®Google Scholar
• De Kimpe N, De Cock W, Keppens M, De Smaele D, Mészáros A. Synthesis of 2-imino-4-thiazolines, 2-imino-4-alkoxythiazolidines, thiazoles and 4-imidazolin-2-ones from α-halomethyl ketimines. J Heterocycl Chem. 1996;33:1179–1183. doi: 10.1002/jhet.5570330429
   Web of Science ®Google Scholar
• Castro R, Garcia-vazquez JA, Romero J, Sousa A. Electrochemical synthesis of benzothiazole-2-thionato complexes of nickel (II), zinc(II) and cadmium(II): the crystal structure of 2,2′-bipyridine bis(benzothiazole-2-thionato)zinc(II). Polyhedron. 1993;12:2241–2247. doi: 10.1016/S0277-5387(00)88263-7
   Web of Science ®Google Scholar
• Castro JA, Romero J, Garcia-Vazquez JA, Sousa A, Castellano EE, Zukerman-Schpector J. Electrochemical synthesis of cadmium(II) complexes of Schiff bases: the crystal structure of 2,2′-bipyridine bis {2-[2-methoxyphenyl)-iminomethyl]-pyrrolato}cadmium(II). Polyhedron. 1993;12:31–36. doi: 10.1016/S0277-5387(00)87050-3
   Web of Science ®Google Scholar
• Mague JT, Mohamed SK, Akkurt M, Hassan AA, Albayati MR. Crystal structure of 2-[(E)-2-(2-chlorobenzylidene)hydrazin-1-yl]-4-phenyl-1,3-thiazole. Acta Cryst. 2014;E70:0907–0908.
   Google Scholar
• Tišler M. 4-Phenylthiosemicarbazid als reagens zur charakterisierung von aldehyden und ketonen. Fresenius Zeit Schrif Für Analytische Chemie. 1956;149:164–172. doi: 10.1007/BF00585763
   Web of Science ®Google Scholar
• Venkatramau R, Davis K, Shelby A, Zubkowski JD, Valente EJ. syn, E-1-cyclopentano-4-ethyl-3-thiosemicarbazone and syn,E-1-cyclopentano-4-phenyl-3-thiosemicarbazone. J Chem Cryst. 1999;29:429–434. doi: 10.1023/A:1009515111029
   Web of Science ®Google Scholar
• Mague JT, Mohamed SK, Akkurt M, Hassan AA, Albayati MR. (2E)-4-(4-Bromophenyl)-2-{2-[(1E)-cyclopentylidene]hydrazin-1-ylidene}-3-phenyl-2,3-dihydro-1,3-thiazole. Acta Cryst. 2014;E70:0669–0669.
   Google Scholar
• Bruker. APEX2, SAINT, SADABS, SHELXT and SHELXTL, Madison, WI: Bruker AXS, Inc.; 2014.
   Google Scholar
• Sheldrick GM. SHELXL–2014. Göttingen: University of Göttingen; 2014.
   Google Scholar
• Brandenburg K, Putz H. DIAMOND, Bonn: Crystal Impact GbR; 2012.
   Google Scholar
• Nobuta T, Hirashima S, Tada N, Miura T, Itoh A. One-pot metal-free syntheses of acetophenones from styrenes through aerobic photo-oxidation and deiodination with iodine. Org Lett. 2011;13:2576–2579. doi: 10.1021/ol200681k
   PubMed Web of Science ®Google Scholar
• Salama TA, Novák Z. N-Halosuccinimide/SiCl4 as general, mild and efficient systems for the α-monohalogenation of carbonyl compounds and for benzylic halogenations. Tetrahedron Lett. 2011;52:4026–4029. doi: 10.1016/j.tetlet.2011.05.135
   Web of Science ®Google Scholar
• Varsha J, Pradeep M, Sushil LK, Stables JP. Synthesis and CNS depressant activity of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones. Eur J Med Chem. 2008;43:135–141. doi: 10.1016/j.ejmech.2007.02.004
   PubMed Web of Science ®Google Scholar