Synthesis of thiazoles and aminothiazoles from β-keto tosylates under supramolecular catalysis in the presence of β-cyclodextrin in water

Synthetic Communications

Volumn 37, Issue 24, 2007, Pages 4331-4336

  Kumar, V Pavan ^a   Narender, M ^a   Sridhar, R ^a   Nageswar, Y V D ^a   Rao, K Rama ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

cyclodextrin; keto tosylate; Aminothiazoles; Supramolecular catalysis; Thiazoles; Thioamide; Thiourea; Water

Indexed keywords

4 TERT BUTYL 2 METHYLTHIAZOLE; 4 TERT BUTYL 2 PHENYLTHIAZOLE; 4 TERT BUTYLTHIAZOL 2 AMINE; BETA CYCLODEXTRIN; THIAZOLE DERIVATIVE; THIOAMIDE; THIOUREA; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 37249023009     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701575913     Document Type: Article

References (28)

1. (a) Benazzouz, A.; Boraud, T.; Dubedat, P.; Boireau, A.; Stutzmann, J.-M.; Gross, C. Riluzole prevents MPTP-induced parkinsonism in the rhesus monkey: a pilot study. Eur. J. Pharmacol 1995, 284, 299;
2. (b) Jimonet, P.; Audiau, F.; Barreau, M.; Blanchard, J.-C.; Boireau, A.; Bour, Y.; Coleno, M.-A.; Doble, A.; Doerflinger, G.; Huu, C. D.; Donat, M.-H.; Duchesne, J. M.; Ganil, P.; Gueremy, C.; Honore, E.; Just, B.; Kerphirique, R.; Gontier, S.; Hubert, P.; Laduron, P. M.; Blevec, J. L.; Meunier, M.; Miquet, J.-M.; Nemecek, C.; Pasquet, M.; Piot, O.; Pratt, J.; Rataud, J.; Reibaud, M.; Stutzmann, J.-M.; Mignani, S. Riluzole series. Synthesis and in vivo "Antiglutamate", activity of 6-substituted-2-benzothiazolamines and 3-substituted-2-imino-benzothiazolines benzothiazolines as antituberculous agents. J. Med. Chem. 1999, 42, 2828.
3. Palmer, P. J.; Trigg, R. B.; Warrington, J. V. Benzothiazolines as antituberculous agents. J. Med. Chem. 1971, 14, 248.
4. Patt, W. C.; Hamilton, H. W.; Taylor, M. D.; Ryan, M. J.; Taylor, D. G. Jr.; Connolly, C. J. C.; Doharty, A. M.; Klutchko, S. R.; Sircar, I.; Steinbaugh, B. A.; Bately, B. L.; Painchand, C. A.; Rapundalo, S. T.; Michniewicz, B. M.; Olzon, S. C. J. Structure-activity relationships of a series of 2-amino-4-thiazole-containing renin inhibitors. J. Med. Chem. 1992, 35, 2562.
5. (a) Haviv, F.; Ratajczyk, J. D.; DeNet, R. W.; Kerdesky, F. A.; Walters, R. L.; Schmidt, S. P.; Holms, J. H.; Young, P. R.; Carter, G. W. 3-[1-(2-Benzoxazolyl)-hydrazino] propane nitrile derivatives: inhibitors of immune complex induced inflammation. J. Med. Chem. 1988, 31, 1719;
6. (b) Clemence, F.; Marter, O. L.; Delevalle, F.; Benzoni, J.; Jouanen, A.; Jouquey, S.; Mouren, M.; Deraedt, R. 4-Hydroxy-3-quinolinecarboxamides with antiarthritic and analgesic activities. J. Med. Chem 1988, 31, 1453.
7. Ivanov, S. K.; Yuritsyn, V. S. Inhibiting action of organic sulfur compounds during cumin oxidation. Neftekhimiya 1971, 11, 99;
8. Chem. Abstr. 1971, 74, 124487 m.
9. (a) Mylari, B. L.; Larson, R.; Beyer, T. A.; Zembrowski, W. J.; Aldinger, C. E.; Dee, M. F.; Siegel, T. W.; Singleton, D. H. Novel, potent aldose reductase inhibitors: 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2- benzothiazolyl]methyl]-1-phthalazineacetic acid (zopolrestat) and congeners. J. Med. Chem 1991, 34, 108;
10. (b) Kotani, T.; Nagaki, Y.; Ishii, A.; Konishi, Y.; Yago, H.; Suehiro, S.; Okukado, N.; Okamoto, K. Highly selective Aldose reductase inhibitors. 3. Structural diversity of 3-(arylmethyl)-2,4,5-trioxoimidazolidine-1-acetic acids. J. Med. Chem. 1997, 40, 684.
11. (a) Hadjipavlou-Litina, D. J.; Geronikaki, A. A. Thiazolyl and benzothiazolyl Schiff bases as novel possible lipoxygenase inhibitors and anti inflammatory agents. Synthesis and biological evaluation. Drug Des. Discovery 1998, 15, 199;
12. (b) Oketani, K.; Inoue, T.; Murakami, M. Effect of E3040, an inhibitor of 5-lipoxygenase and thromboxane synthase, on rat bowel damage induced by lipopolysaccharide. Eur. J. Pharmacol. 2001, 427, 159.
13. Nagel, A. A.; Liston, D. R.; Jung, S.; Mahar, M.; Vincent, L. A.; Chapin, D.; Chen, Y. L.; Hubbard, S.; Ives, J. L.; Jones, S. B. Design and synthesis of 1-heteroaryl-3-(1-benzyl-4-piperidinyl)propan-1-one derivatives as potent, selective acetylcholinesterase inhibitors. J. Med. Chem 1995, 38, 1084.
14. + ATPase inhibitor, YJA20379-1,2-amino-4, 5-dihydro-8-phenylimidazole[ 2,1-b]thiazolo[5,4-g]benzothiazole. Can. J. Physiol. Pharmacol. 1999, 77, 330.
15. Phoon, C. W.; Ng, P. Y.; Ting, A. E.; Yeo, S. L.; Sim, M. M. Biological evaluation of hepatitis c virus helicase inhibitors. Bioorg. Med. Chem. Lett. 2001, 11, 1647.
16. (a) Baxter, A. D. Synthesis utilizing insoluble polymers: new reactions and small molecules. Curr. Opin. Chem. Biol. 1997, 1, 79;
17. (b) Rich, D. H.; Wiley, R. A. Peptidomimetics derived from natural products. Med. Res. Rev. 1993, 13, 327;
18. (c) Kearney, P. C.; Fernandez, M.; Flygare, J. A. Solid-phase synthesis of 2-aminothiazoles. J. Org. Chem. 1998, 63, 196;
19. (d) Goff, D.; Fernandez, J. The preparation of 2,4-disubstituted thiazoles on solid support. Tetrahedron Lett. 1999, 40, 423.
20. (a) Surendra, K.; Krishnaveni, N. S.; Rao, K. R. Study of the Michael addition of β-cyclodextrin-thiol complexes to conjugated alkenes in water. Chem. Commun. 2005, 669;
21. (b) Krishnaveni, N. S.; Surendra, K.; Rao, K. R. A simple and highly selective biomimetic oxidation of alcohols and epoxides with N-bromosuccinimide in the presence of β-cyclodextrin in water. Adv. Synth. Catal. 2004, 346, 346;
22. (c) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. Highly selective oxidative cleavage of β-cyclodextrin-epoxide/ aziridine complexes with IBX in water. J. Org. Chem. 2003, 68, 9119;
23. (d) Surendra, K.; Krishnaveni, N. S.; Nageswar, Y. V. D.; Rao, K. R. Highly regioselective ring opening of oxiranes with phenoxides in the presence of β-cyclodextrin in water. J. Org. Chem. 2003, 68, 4994;
24. (e) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. Mild oxidation of alcohols with o-Iodoxybenzoic Acid (IBX) in water/acetone mixture in the presence of β-cyclodextrin. J. Org. Chem. 2003, 68, 2058.
25. Schneider, H. J.; Hacket, F.; Rudiger, V.; Ikeda, H. NMR studies of cyclodextrins and cyclodextrin complexes. Chem. Rev. 1998, 98, 1755.
26. Demarco, P. V.; Thakkar, A. L. Cyclohepta-amylose inclusion complexes. A proton magnetic resonance study. J. Chem. Soc. Chem. Commun. 1970, 2.
27. (a) Ukema, K.; Hirayama, F.; Irie, T. Cyclodextrin drug carrier systems. Chem. Rev. 1998, 98, 2045;
28. (b) Szejtli, J. In Comprehensive Supramolecular Chemistry, Szejtli, J., and Osa, T., Eds.; Pergamon: Oxford, 1991 Vol. 3, pp. 5.