A one-pot four-component synthesis of 3-[(2-amino-4-arylthiazolium-5-yl)(aryl)methyl]-2-oxo-2H-1-benzopyran-4-olates

References

• Tietze LF, Beifuss U. Sequential transformations in organic chemistry: A synthetic strategy with a future. Angew Chem. Int Ed. 1993;32:131–163. doi: 10.1002/anie.199301313
   Web of Science ®Google Scholar
• Padwa A, Bur SK. The domino way to heterocycles. Tetrahedron. 2007;63:5341–5378. doi: 10.1016/j.tet.2007.03.158
   PubMed Web of Science ®Google Scholar
• Pellissier H. Asymmetric domino reactions. part A: reactions based on the use of chiral auxiliaries. Tetrahedron. 2006;62:1619–1665. doi: 10.1016/j.tet.2005.10.040
   Web of Science ®Google Scholar
• Nicolaou KC, Edmonds DJ, Bulger PG. Cascade reactions in total synthesis. Angew Chem, Int Ed Engl. 2006;45:7134–7186. doi: 10.1002/anie.200601872
   PubMed Web of Science ®Google Scholar
• Tietze LF. Domino reactions in organic synthesis. Chem Rev. 1996;96:115–136. doi: 10.1021/cr950027e
   PubMed Web of Science ®Google Scholar
• Majnooni S, Duffield J, Price J, et al. Aryliodoazide synthons: A different approach for diversified synthesis of 2-aminothiazole, 1,3-thiazole, and 1,3-selenazole scaffolds. ACS Comb Sci. 2019;21:516–521. doi: 10.1021/acscombsci.9b00045
   PubMed Web of Science ®Google Scholar
• Keshari T, Kapoorr R, Yadav LDS. Carbon tetrabromide mediated oxidative cyclocondensation of ketones and thioureas: an easy access to 2-aminothiazoles. Tetrahedron Lett. 2015;56:5623–5627. doi: 10.1016/j.tetlet.2015.08.064
   Web of Science ®Google Scholar
• Banothu J, Vaarla K, Bavantula R, et al. Sodium fluoride as an efficient catalyst for the synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles at ambient temperature. Chin Chem Lett. 2014;25:172–175. doi: 10.1016/j.cclet.2013.10.001
   Web of Science ®Google Scholar
• Narender M, Reddy MS, Sridhar R, et al. 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
• 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
• 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
• Donohoe T, Kabeshov MA, Rathi AH, et al. Direct preparation of heteroaromatic compounds from alkenes. Synlett. 2010;2010:2956–2958. doi: 10.1055/s-0030-1259034
   Web of Science ®Google Scholar
• Ma C, Miao Y, Zhao M, et al. Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH). Tetrahedron. 2018;74:3602–3607. doi: 10.1016/j.tet.2018.05.021
   Web of Science ®Google Scholar
• Karade H, Sathe M, Kaushik MP. An efficient method for the synthesis of 2-aminothiazoles using silica chloride as a heterogeneous catalyst. Catal Commun. 2007;8:741–746. doi: 10.1016/j.catcom.2006.09.005
   Web of Science ®Google Scholar
• Abedi-Jazini Z, Safari J, Zarnegar Z, et al. A simple and efficient method for the synthesis of 2-aminothiazoles under mild conditions. Polycyclic Arom Compd. 2018;38:231–235. doi: 10.1080/10406638.2016.1200104
   Web of Science ®Google Scholar
• Yavari I, Saffarian H, Naeimabadi M. A one-pot synthesis of novel cyclic ketene dithioacetals from Nef-isocyanide Perkow adduct. J Sulfur Chem. 2017;38:679–685. doi: 10.1080/17415993.2017.1347173
   Web of Science ®Google Scholar
• Diyanatizadeh MH, Yavari I. A synthesis of functionalized spiro isobenzofuran-1,6′-[1,3] thiazines from phthalic anhydride-malononitrile adduct and ammonium carbamodithioates. J Sulfur Chem. 2016;37:54–60. doi: 10.1080/17415993.2015.1089439
   Web of Science ®Google Scholar
• Yavari I, Taheri Z, Naeimabadi M, et al. A convenient synthesis of Tetrasubstituted Pyrazoles from Nitrile Imines and 2-(Thioxothiazolidin-5-ylidene) acetates. Synlett. 2018;29:918–921. doi: 10.1055/s-0036-1591921
   Web of Science ®Google Scholar
• Banothu J, Khanapur M, Basavoju S, et al. Synthesis, characterization and biological evaluation of fused thiazolo[3,2-a]pyrimidine derivatives. RSC Adv. 2014;4:22866–22874. doi: 10.1039/c4ra02514h
   Web of Science ®Google Scholar
• Sakram B, Sonyanaik B, Ashok K, et al. Benzo[h]thiazolo[2,3-b]quinazolines by an efficient p-toluenesulfonic acid-catalyzed one-pot two-step tandem reaction. Res Chem Intermed. 2016;42:1699–1705. doi: 10.1007/s11164-015-2112-4
   Web of Science ®Google Scholar
• Olawode EO, Tandlich R, Prinsloo E, et al. Synthesis and biological evaluation of 2-chloro-3-[(thiazol-2-yl)amino]-1,4-naphthoquinones. Bioorg Med Chem Lett. 2019;29:1572–1575. doi: 10.1016/j.bmcl.2019.05.001
   PubMedGoogle Scholar
• Sravanthi TV, Manju SL. Synthesis and Fluorescence Properties of Novel indol-3yl-thiazolo[3,2-a][1,3,5]triazines and indole-3-carbaldehyde Schiff Bases. J Fluoresc. 2015;25:1727–1738. doi: 10.1007/s10895-015-1659-1
   PubMed Web of Science ®Google Scholar
• Burnett MN, Johnson CK. ORTEP-III Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA 1996.
   Google Scholar
• Sheldrick GM. A short history of SHELX. Acta Crystallogr Sect A. 2008;64:112–122. doi: 10.1107/S0108767307043930
   PubMed Web of Science ®Google Scholar
• Allen FH, Johnson O, Shields GP, et al. CIF applications. XV. EnCIFer: A program for viewing, editing and visualizing CIFs. J Appl Cryst. 2004;37:335–338. doi: 10.1107/S0021889804003528
   Web of Science ®Google Scholar