Convenient one-pot synthesis of 2-oxazolines from carboxylic acids

Chemical and Pharmaceutical Bulletin

Volumn 56, Issue 12, 2008, Pages 1735-1737

  Hioki, Kazuhito ^b   Takechi, Yumiko ^b   Kimura, Noriyo ^b   Tanaka, Hiroyuki ^a   Kunishima, Munetaka ^a,b  

^a KANAZAWA UNIVERSITY   (Japan)

^b KOBE GAKUIN UNIVERSITY   (Japan)

Author keywords

2 haloethylammonium salt; Carboxylic acid; Cyclization; Dehydrocondensation; Oxazoline

Indexed keywords

2 (1 PHENETHYL) 2 OXAZOLINE; 2 (2 PHENETHYL) 2 OXAZOLINE; 2 (2 PHENYLETHENYL) 2 OXAZOLINE; 2 (3 BUTENYL) 2 OXAZOLINE; 2 (N BUTOXYCARBONYL 1 AMINO 2 PHENYLETHYL) 2 OXAZOLINE; 2 CYCLOHEXYL 2 OXAZOLINE; 2 HALOETHYLAMMONIUM DERIVATIVE; 2 OXAZOLINE DERIVATIVE; 2 PHENYL 2 OXAZOLINE; 4 (4,6 DIMETHOXY 1,3,5 TRIAZIN 2 YL) 4 METHYLMORPHOLINIUM CHLORIDE; AMMONIUM DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; METHANOL; OXAZOLINE DERIVATIVE; POTASSIUM HYDROXIDE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DEHYDROCONDENSATION; ONE POT SYNTHESIS; POLYMERIZATION; REPRODUCIBILITY; TECHNIQUE;

CARBOXYLIC ACIDS; HYDROXIDES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; METHANOL; OXAZOLES; POTASSIUM COMPOUNDS; SPECTROPHOTOMETRY, INFRARED;

EID: 57349188917     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.56.1735     Document Type: Article

References (26)

1. Gant T. G., Meyers A. I., Tetrahedron, 50, 2297-2360 (1994).
2. Reuman M., Meyers A. I., Tetrahedron, 41, 837-860 (1985).
3. Meyers A. I., Mihelich E. D., Angew. Chem., 88, 321-332 (1976).
4. Frump J. A., Chem. Rev., 71, 483-506 (1971).
5. Wiley R. H., Bennett L. L. Jr., Chem. Rev., 44, 447-476 (1949).
6. Greene T. W., Wuts P. G. M., "Protective Groups in Organic Synthesis," 2nd ed., John Wiley & Sons, New York, 1991, pp. 265-266.
7. Hamada Y., Shibata M., Shioiri T., Tetrahedron Lett., 26, 6501-6504 (1985).
8. Lusskin R. M., Ritter J. J., J. Am. Chem. Soc., 72, 5577-5578 (1950).
9. Fry E. M., J. Org. Chem., 14, 887-894 (1949).
10. Kashima C., Arao H., Synthesis, 1989, 873-874 (1989).
11. Jakisch L., Böhme F., Komber H., Pompe G., Macromol. Rapid Commun., 20, 256-260 (1999).
12. Hunt D. A., Org. Prep. Proced. Int., 39, 93-96 (2006).
13. Kunishima M., Kawachi C., Morita J., Terao K., Iwasaki F., Tani S., Tetrahedron, 55, 13159-13170 (1999).
14. Kunishima M., Kawachi C., Hioki K., Terao K., Tani S., Tetrahedron, 57, 1551-1558 (2001).
15. Ghosh A. K., Mathivanan P., Cappiello J., Tetrahedron: Asymmetry, 9, 1-45 (1998).
16. Schaefer F. C., J. Am. Chem. Soc., 77, 5928-5930 (1955).
17. Prolongation of refluxing time with an excess KOH caused partial racemization (ca. 5%).
18. Pirrung M C., Tumey L. N., J. Comb. Chem., 2, 675-680 (2000).
19. Ishihara M., Togo H., Tetrahedron, 63, 1474-1480 (2006).
20. Cherton J.-C., Beaufour M., Menguy L., Merelli B., Spectrosc. Lett., 35, 415-437 (2002).
21. Terao K., Takechi Y., Kunishima M., Tani S., Ito A., Yamasaki C., Fukuzawa S.-I., Chem. Lett., 2002, 522-523 (2002).
22. Beutler A., Davies C. D., Elliott M. C., Galea N. M., Long M. S., Willock D. J., Wood J. L., Eur. J. Org. Chem., 2005, 3791-3800 (2005).
23. Ishihara M., Togo H., Tetrahedron, 63, 1474-1480 (2006).
24. Galeotti N., Montagne C., Poncet J., Jouin P., Tetrahedron Lett., 33, 2807-2810 (1992).
25. Ohshima T., Iwasaki T., Mashima K., Chem. Commun., 2006, 2711-2713 (2006).
26. Kurth M. J., Decker O. H. W., Hope H., Yanuck M. D., J. Am. Chem. Soc., 107, 443-448 (1985).