The preparation of 2-(4-oxo-4h-1-benzopyran-2-yl)- 1-phenylethanones by the condensation/cyclization of dilithiated 1-benzoylacetone with lithiated methyl salicylates

Synthetic Communications

Volumn 28, Issue 9, 1998, Pages 1547-1554

  Angel, April J ^a   Hurst, Douglas R ^a   Williams, Angela R ^a   French, Kristen L ^a   Beam, Charles F ^a  

^a Department of Teacher Education and Department of Sociology and Anthropology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 OXO 4H 1 BENZOPYRAN 2 YL) 1 PHENYLETHANONE; ACETONE; BENZOPYRAN DERIVATIVE; LITHIUM; SALICYLIC ACID METHYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FOURIER TRANSFORMATION; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0031955120     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808006858     Document Type: Article

References (22)

1. Beam, C.F., Hines, M.A., Mazat, C.L., Duncan, D.C., Beckman, D.D., Lachicotte, R.J., Tummons, R.C., and Heindel, N.D., Chem. and Indust. (London), 1989, 727.
2. b. Livingston, M.L., Chick, M.F., Shealy, E.O., Park, D.J., Fulmer, T.D., and Beam, C.F., J. Heterocycl. Chem., 1982, 19, 215.
3. c. Beam, C.F., Hall, H.L., Huff, A.M., Tummons, R.C., O'Grady, S.A., J. Heterocycl. Chem., 1984, 21, 1897.
4. d. Mazat, C.L., Beam, C.F., and Hines, M.A., Synthetic Communications., 1990, 20, 253.
5. Costa, A.M.B.S.R.C.S., Dean, F.M., Jones, M.A., Sons, M.A., and Smith, D.A. J. Chem. Soc., Perkin Trans. 1 1986, 1707.
6. a. Hauser, C.R., and Harris, T.M., J. Amer. Chem. Soc., 1958, 80, 6360.
7. b. Light, R.J., and Hauser, C.R., J. Org. Chem., 1960, 25, 538.
8. c. von Schrilz, D.M., Miles, M.L., and Hauser, C.R., J. Org. Chem., 1967, 32, 1774.
9. Hepworth, J.P. "Comprehensive Heterocyclic Chemistry", Vol. 3. Part 2B, Katritzky, A.R. and Rees, C.W., Ed. Board, Pergamon Press, New York, New York, 1984, pp 816-830.
10. a. Rogalski, W., Kirchlechner, R., Seubert, J., Gottschlich, R., Steinieweg, R., Bergmann, R., and Wahlig, H., Ger. Offen. 1976, DE 2,442,829; Chem. Abstr., 1976 85, P5501d.
11. b. Eiden, F., Rademacher, R., and Schuenemann, J., Arch. Pharm. (Weinheim Ger.) 1984, 317, 539.
12. c. Nixon, N.S., Scheinmann, F., and Suschitzky, J.L., Tetrahedron Lett. 1983, 24, 597.
13. d. Bringmann, G., and Schneider, S., Liebigs Ann. Chem. 1985, 765.
14. e. Jamura, Y., Tsugoshi, T., Morhi, S., and Kita, Y., J. Org. Chem. 1985, 50, 1542.
15. f. Huang, F.C., Campbell, H.F., Learn, K.S., and Gammon, Jr., R.A., U.S. Patent, 1989, US 4,977,162; Chem. Abstr. 1991, 115, P8594k.
16. g. Gammill, R.B., Nash, S.A., Bell, L.T., and Watt, W., Tetrahedron Lett. 1992, 33, 993.
17. h. Morin, C., and Beugelmans, R., Tetrahedron Lett. 1977, 33, 3183.
18. i. Doad, G.J.S., Okar, D.I. Scheinmann, F., Bates, P.A., and Hursthouse, M.B., J. Chem. Soc., Perkin Trans. 1 1988, 22993.
19. 2-), 6.42 and 6.52 (s, vinyl), 6.58-7.15 and 7.50-8.33 (m, ArH).
20. 6). See also: a. ref. 1b. b. Brown, J., Sides, K.L., Fulmer, T.D., and Beam, C.F., J. Heterocycl. Chem., 1979, 16, 1669. c. Huff, A.M., Hall, H.L., Smith, M.J., O'Grady, S.A., Waters, F.C., Fengl, R.W., Welch, J.A., and Beam, C.F., J. Heterocycl. Chem., 1985, 22, 501.
21. 6). See also: a. ref. 1b. b. Brown, J., Sides, K.L., Fulmer, T.D., and Beam, C.F., J. Heterocycl. Chem., 1979, 16, 1669. c. Huff, A.M., Hall, H.L., Smith, M.J., O'Grady, S.A., Waters, F.C., Fengl, R.W., Welch, J.A., and Beam, C.F., J. Heterocycl. Chem., 1985, 22, 501.
22. 6). See also: a. ref. 1b. b. Brown, J., Sides, K.L., Fulmer, T.D., and Beam, C.F., J. Heterocycl. Chem., 1979, 16, 1669. c. Huff, A.M., Hall, H.L., Smith, M.J., O'Grady, S.A., Waters, F.C., Fengl, R.W., Welch, J.A., and Beam, C.F., J. Heterocycl. Chem., 1985, 22, 501.