3,5-diarylisoxazoles: Individualized three-step synthesis and isomer determination using 13C NMR or mass spectroscopy

Journal of Chemical Education

Volumn 83, Issue 9, 2006, Pages 1336-1340

  Stephens, Chad E ^a,b   Arafa, Reem K ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

^b AUGUSTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

CHALCONE SYNTHESIS; DIARYLISOXAZOLES; ISOMER DETERMINATION; MASS SPECTROSCOPY; THREE-STEP SYNTHESIS;

CHEMISTRY;

EID: 33748260588     PISSN: 00219584     EISSN: None     Source Type: Journal    
DOI: 10.1021/ed083p1336     Document Type: Article

References (27)

1. Vyvyan, J. R.; Pavia, D. L.; Lampman, G. M.; Kriz, G. S. J. Chem. Educ. 2002, 79, 1119.
2. Pond, F. J.; York, H. J.; Moore, B. L. J. Am. Chem. Soc. 1901, 23, 789.
3. (a) Moloney, G. P. J. Chem. Educ. 1990, 67, 617.
4. (b) Dixon, C. E.; Pyne, S. G. J, Chem. Educ. 1992, 69, 1032.
5. The Chemistry of Heterocycles. Isoxazoles, Part 1; Taylor, E. C., Ed.; John Wiley & Sons: New York, 1991.
6. Baumstark, A. L.; Chrisope, D. R.; Keel, R. A.; Boykin, D. W. J. Heterocycl. Chem. 1980, 17, 1719.
7. Raiford, L. C.; Davis, H. L. J. Am. Chem. Soc. 1928, 50, 126.
8. Organic Chemistry Faculty. Chemistry 3110 Lab Manual; Georgia State University: Atlanta, 1998.
9. Balaban, A. T.; Oniciu, D. C.; Katritzky, A. R. Chem. Rev. 2004, 104, 2777.
10. The limited number of heterocyclic syntheses in the undergraduate curriculum has previously been noted in this Journal: Seaton, P. J.; Williamson, R. T. J. Chem. Educ. 2002, 79, 106.
11. A related isoxazoline synthesis has recently appeared in this Journal: Martin, W. B.; Kateley, L. J.; Wiser, D. C.; Brummond, C. A. J. Chem. Educ. 2002, 79, 225.
12. Pevarello, P.; Amici, R.; Brasca, M. G.; Villa, M.; Varasi, M. Recent Applications of the Isoxazole Ring in Medicinal Chemistry. In Targets in Heterocyclic Chemistry; Attanasi, O. A., Spinelli, D., Eds.; Italian Society of Chemistry: Rome, 1999; Vol. 3, pp 301-339.
13. Mohrig, J. R. J. Chem. Educ. 2004, 81, 1083.
14. (a) Wachter-Juresak, N.; Zamani, H. J. Chem. Educ. 1999, 76,653.
15. (b) Palleros, D. R. J. Chem. Educ. 2004, 81, 1345.
16. Hayamizu, K.; Yanagisowa, M.; Ishii, T.; Yabe, A.; Yamamoto, O.; Nakayama, M.; Hayashi, A. Mag. Res. Chem. 1989, 27, 899.
17. Student use of the Beilstein database has recently been discussed in this Journal: Christensen, S. B.; Franzyk, H.; Frolund, B.; Jaroszewski, J. W.; Staerk, D.; Vedso, P. J. Chem. Educ. 2002, 79, 765.
18. Rekhter, M. A.; Grushetskaya, G. N.; Panasenko, A. A.; Krimer, M. Z. Chem. Heterocycl. Compds. 1995, 31, 792.
19. Lutz, R. E.; Hinkley, D. F.; Jordan, R. H. J, Am. Chem. Soc. 1951, 73, 4647.
20. Thakare, S. S.; Doshi, A. G. Asian J. Chem. 2001, 13, 780.
21. Khatyr, A.; Maas, H.; Calzaferri, G. J. Org. Chem. 2002, 67, 6705.
22. Battaglia, A.; Dondoni, A.; Taddei, F. J. Heterocycl. Chem. 1970, 7, 721.
23. Chrisope, D. R.; Keel, R. A.; Baumstark, A. L.; Boykin, D. W. J. Heterocycl. Chem. 1981, 18, 795.
24. Barnes, R. P.; Dodson, L. B. J. Am. Chem. Soc. 1945, 67, 132.
25. For an extensive list of Hammett constants, see: Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani, D.; Lien, E. J. J. Med. Chem. 1973, 16, 1207. For an experiment relating the chemical shift of the vinyl protons of chalcones to substituent Hammett constants, see ref 13a.
26. 13C NMR substituent shift-effect constant, see either of the following: (a) Levy, G. C; Lichter, R. L.; Nelson, G. L. Carbon-13 Nuclear Magnetic Resonance Spectroscopy, 2nd ed.; John Wiley & Sons: New York, 1980; Table 4.3.
27. (b) Pretsch, E.; Buhlmann, P.; Affolter C. Structure Determination of Organic Compounds; Springer-Verlag: Berlin, 2000; p 97.