Solid-phase synthesis of 4H-2-(3-hydroxy-4-methoxyphenyl)-naphtho[1,2-b] pyran-1-one

Tetrahedron Letters

Volumn 45, Issue 39, 2004, Pages 7311-7314

  Cironi, Pablo ^a   Albericio, Fernando ^a   Álvarez, Mercedes ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Chromones; Heterocycles; Naphthopyrones; Solid phase synthesis

Indexed keywords

4H 2 (3 HYDROXY 4 METHOXYPHENYL)NAPHTHO[1,2 B]PYRAN 1 ONE; ACETYLCHOLINE DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

CONFERENCE PAPER; DRUG SYNTHESIS; METHODOLOGY; SOLID;

EID: 4444227437     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.012     Document Type: Conference Paper

References (20)

1. F. Toda Kagaku 44 1989 312 317
2. P. Iyer, and S.K. Ghosh Tetrahedron Lett. 43 2002 9437 9440
3. P. Cironi, F. Albericio, and M. Álvarez G.W. Gribble J.A. Joule Progress in Heterocyclic Chemistry Vol. 16 2004 Pergamon Oxford, UK 1 26 Chapter 1
4. P. Cironi, I. Manzanares, F. Albericio, and M. Álvarez Org. Lett. 5 2003 2959 2962
5. This strategy was first used in solution by: M. Banwell, B. Flynn, and D. Hockless Chem. Commun. 1997 2259 2260
6. 3
7. + 212.0840
8. P. Cironi, J. Tulla-Puche, G. Barany, F. Albericio, and M. Álvarez Org. Lett. 6 2004 1405 1408
9. 3) 56.0, 56.4, 70.9, 80.0, 94.0, 95.6, 111.4, 116.7, 148.0, 149.9
10. Similar reaction conditions gave good results in solution: A.S. Droz, U. Neidlein, S. Anderson, P. Seiler, and F. Diederich Helv. Chim. Acta 84 2001 2243 2289
11. J.W. Huffman, X. Zhang, M.-J. Wu, H.H. Joyner, and W.T. Pennington J. Org. Chem. 56 1991 1481 1489
12. The absence of these absorptions was not considered significant because they are frequently not observed in bisarylacetylenes
13. Cleavage of 80 mg of 7 gave a crude product, which was purified by HPLC to afford 8 (6 mg, 43% overall yield) and 9 (1 mg, 7% overall yield)
14. + found 318.0892
15. + found 353.0575
16. A precedent for the chlorination of a similar aromatic ring was previously described by: Cironi, P.; Cuevas, C.; Albericio, F.; Álvarez, M. Tetrahedron, 2004, 60, in press. doi:10.1016/j.tet.2004.05.119
17. A SciFinder search showed just 11 references containing the 2-(aryl)naphtho[1,2-b]pyran-1-one
18. Also known as 3-(aryl)benzo[f]chromone
19. Chromones have been described as inhibitors of phosphatidylinositol 3′-kinase in human colon cancer cells by: S. Sembra, M. Itoh, M. Harada, and M. Yamakawa Clin. Cancer Res. 8 2002 1957 1963; as hypoglycemic agents by: R.R. Reddy, and V.M. Reddy Indian Drugs 34 1997 258-263; for preventing asthmatic symptoms by: Kllutchko, S.; Brown, R. E.; Von Strandtmann, M. (Warner-Lambert CO., USA) US 74-504628 19740909
20. Chromones have been described as inhibitors of phosphatidylinositol 3′-kinase in human colon cancer cells by: S. Sembra, M. Itoh, M. Harada, and M. Yamakawa Clin. Cancer Res. 8 2002 1957 1963; as hypoglycemic agents by: R.R. Reddy, and V.M. Reddy Indian Drugs 34 1997 258-263; for preventing asthmatic symptoms by: Kllutchko, S.; Brown, R. E.; Von Strandtmann, M. (Warner-Lambert CO., USA) US 74-504628 19740909