Liquid-Phase Organic Synthesis of Thiazoles Using Poly(ethylene glycol)–Bound Sulfonyl Chloride Resin

REFERENCES

• (a) Dolle , R. E. ; Nelson , K. H. Comprehensive survey of combinatorial library synthesis: 1998 . J. Comb. Chem. 1999 , 1 ( 4 ), 235 – 282 ; (b) Dolle, R. E. Comprehensive survey of combinatorial library synthesis: 2000. J. Comb. Chem. 2001, 3(6), 477–517; (c) Dolle, R. E. Comprehensive survey of combinatorial library synthesis: 2002. J. Comb. Chem. 2003, 5(6), 693–753.
   PubMed Web of Science ®Google Scholar
• For a review see (a) Gravert , D. J. ; Janda , K. D. Organic synthesis on soluble polymer supports: Liquid-phase methodologies . Chem. Rev. 1997 , 97 ( 2 ), 489 – 510 ; (b) Wentworth, P.; Janda, K. D. Liquid-phase chemistry: Recent advances in soluble polymer-supported catalysts, reagents, and synthesis. Chem. Commun. 1999, 19, 1917–1924; (c) Toy, P. H.; Janda, K. D. Soluble polymer-supported organic synthesis. Acc. Chem. Res. 2000, 33(8), 546–554; (d) Sun, C. M. Soluble polymer-supported synthesis of heterocyclic libraries. In Combinatorial Chemistry Methods and Protocols; Bellavance L. (Ed.); Humana Press Inc.: NJ, 2002; Chap. 10, pp. 345–371, 546.
   PubMed Web of Science ®Google Scholar
• Franzėn, R. G. Recent advances in the preparation of heterocycles on solid support: A review of the literature . J. Comb. Chem. 2000 , 2 ( 3 ), 195 – 214 .
   PubMed Web of Science ®Google Scholar
• Shey , J. ; Cun , C. M. Liquid-phase combinatorial reaction monitoring by conventional 1H NMR spectroscopy . Tetrahedron Lett. 2002 , 43 ( 9 ), 1725 – 1729 .
   Web of Science ®Google Scholar
• Fink , B. A. ; Mortensen , D. S. ; Stauffer , S. R. ; Aron , Z. D. ; Katzenellenbogen , J. A. Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens . Chem. Biol. 1999 , 6 ( 4 ), 205 – 219 .
   PubMed Web of Science ®Google Scholar
• Van Muijlwijk-Koezen , J. E. ; Timmerman , H. ; Vollinga , R. C. ; Von Drabbe Künzel , J. F. ; De Groote , M. ; Visser , S. ; Ijzerman , A. P. Thiazole and thiadiazole analogues as a novel class of adenosine receptor antagonists . J. Med. Chem. 2001 , 44 ( 5 ), 749 – 762 .
   PubMed Web of Science ®Google Scholar
• Metzger , J. V. Comprehensive Heterocyclic Chemistry I ; New York: Pergamon Press , 1984 ; Vol. 6 , p. 328 .
   Google Scholar
• (a) Ball , C. P. ; Barrett , A. G. M. ; Commercon , A. ; Compère , D. ; Kuhn , C. ; Roberts , R. S. ; Smith , M. L. ; Venier , O. Chameleon catches in combinatorial chemistry: Tebbe olefination of polymer-supported esters and the synthesis of amines, cyclohexanones, enones, methyl ketones, and thiazoles . Chem. Commun. 1998 , 18 , 2019 – 2020 ; (b) Kearney, P. C.; Fernandez, M.; Flygare, J. A. Solid-phase synthesis of 2-aminothiazoles.J. Org. Chem. 1998, 63(1), 196–200; (c) Goff, D.; Fernandez, J. The preparation of 2,4-disubstituted thiazoles on solid support. Tetrahedron Lett. 1999, 40(3), 423–426; (d) Kazzouli, S. E.; Berteina-Raboin, S.; Mouaddib, A.; Guillaumet, G. Solid support synthesis of 2,4-disubstituted thiazoles and aminothiazoles. Tetrahedron Lett. 2002, 43(17), 3193–3196; (e) Okonya, J. F.; Al-Obeidi, F. Synthesis of 2,5-dihalothiazole-4-carboxylates. Tetrahedron Lett. 2002, 43(39), 7051–7053; (f) Stieber, F.; Mazitschek, R.; Soric, N.; Giannis, A.; Waldmann, H. Traceless solid-phase synthesis of 2-aminothiazoles: receptor tyrosine kinase inhibitors with dual selectivity for Tie-2 and VEGFR-2. Angew. Chem. Int. Ed. 2002, 41(24): 4757–4761; (g) Katritzky, A. R.; Cai, X.; Rogovoy, B. V. Solid phase synthesis and application of trisubstituted thioureas. J. Comb. Chem. 2003, 5(4), 392–399; (h) Ueno, M.; Togo, H. Environmentally benign preparation of heteroaromatics from ketones or alcohols, with macroporous polystyrenesulfonic acid and (diacetoxyiodo)benzene, followed by thioamide, amidine, and 2-aminopyridine. Synthesis 2004, 16, 2673–2677. (i) Lee, I. Y.; Lee, J. Y.; Lee, H. J.; Gong, Y.-D. Traceless solid-phase synthesis of 2,4,5-trisubstituted thiazoles. Synlett 2005, 16, 2483–2485.
   Google Scholar
• Wang , Q.-Y. ; Sheng , S.-R. ; Wei , M.-H. ; Xie , Z.-L. ; Liu , X.-L. PEG-supported sulfonic acid as an efficient and recyclable catalyst for the synthesis of 1,1-diacetates under solvent-free conditions. Synth. Commun. 2007, 37(6), 1019–1026.
   Web of Science ®Google Scholar
• (a) Sieber , F. ; Wentworth , P. ; Toker , J. D. ; Wentworth , A. D. ; Metz , W. A. ; Reed , N. N. ; Janda , K. D. Development and application of a poly(ethylene glycol)–supported triarylphosphine reagent: Expanding the sphere of liquid-phase organic synthesis . J. Org. Chem. 1999 , 64 ( 14 ), 5188 – 5192 ; (b) Behrendt, J. M.; Bala, K.; Golding, P.; Hailes, H. C. Oxetane synthesis via cyclisation of aryl sulfonate esters on polystyrene and PEG polymeric supports. Tetrahedron Lett. 2005, 46(4), 643–645.
   PubMed Web of Science ®Google Scholar
• Kar , J. N. ; Acharya , R. C. ; Rout , M. K. Quaternization of thiazoles . J. Org. Chem. 1973 , 38 ( 12 ), 2164 – 2166 .
   Google Scholar
• Graβmann , S. ; Sadek , B. ; Ligneau , X. ; Elz , S. ; Ganellin , C. R. ; Arrang , J. M. ; Schwartz , J. C. ; Stark , H. ; Schunack , W. Progress in the proxifan class: Heterocyclic congeners as novel potent and selective histamine H3-receptor antagonists . Eur. J. Pharm. Sci. 2002 , 15 ( 4 ), 367 – 378 .
   Google Scholar
• Ishida , M. ; Nakanashi , H. ; Kato , S. Novel cyclization of 2-(hydroxymino)-2-phenylethyl dithiocarboxylates . Chem. Lett. 1984 , 13 ( 10 ), 1691 – 1692 .
   Google Scholar
• Maeda , M. ; Kojima , M. Mechanism of the photorearrangements of phenylthiazoles . J. Chem. Soc., Perkin Trans. 1 1978 , 7 , 685 – 692 .
   Google Scholar