Improved synthesis of pyrylium salts leading to 2,4-disubstituted diarylfurans via novel mechanism

Tetrahedron Letters

Volumn 44, Issue 52, 2003, Pages 9271-9274

  Bello, Angélica M ^a   Kotra, Lakshmi P ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE; BENZOIC ACID DERIVATIVE; FURAN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0344010075     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.069     Document Type: Article

References (21)

1. Holla B.S., Shivananda N.K., Shenoy M.S., Antony G. Il Farmaco. 53:1998;531-535.
2. Francesconi I., Wilson W.D., Tanious F.A., Hall J.E., Bender B.C., Tidwell R.R., McCurdy D., Boykin D.W. J. Med. Chem. 42:1999;2260-2265.
3. Boykin D.W., Kumar A., Xiao G., Wilson W.D., Bender B.C., McCurdy D.R., Hall J.E., Tidwell R.R. J. Med. Chem. 41:1998;124-129.
4. Del Poeta M., Schell W.A., Dykstra C.C., Jones S., Tidwell R.R., Czarny A., Bajic M., Kumar A., Boykin D., Perfect J.R. Antimicrob. Agents Chemother. 42:1998;2495-2502.
5. Balachari D., Quinn L., O'Doherty G.A. Tetrahedron. 40:1999;4769-4773.
6. Rodriguez-Saona C.R., Maynard D.F., Phillips S., Trumble J.T. J. Nat. Prod. 62:1999;191-193.
7. Boykin D.W., Kumar A., Spychala J., Zhou M., Lombardy R.J., Wilson W.D., Dykstra C.C., Jones S.K., Hall J.E., Tidwell R.R., Laughton C., Nunn C.M., Neidle S. J. Med. Chem. 38:1995;912-916.
8. Kumar A., Boykin D.W., Wilson W.D., Jones S.K., Bender B.K., Dykstra C.C., Hall J.E., Tidwell R.R. Eur. J. Med. Chem. 31:1996;767-773.
9. Xue L.H., Hui Y.C., Tung Y.H., Po L.K., Ting H.L., Sing Y.T., Wong H.N.C. Tetrahedron. 54:1998;1955-2020.
10. Donelly D.M.X., Meegan M.J. Bird C.W., Cheeseman G.W.H. Comprehensive Heterocyclic Chemistry. 4:1984;657 Pergamon, Oxford.
11. Mortensen D.S., Rodriguez A.L., Sun J., Katzenellenbogen B.S., Katzenellenbogen J.A. Bioorg. Med. Chem. Lett. 11:2001;2521-2524.
12. Mortensen A.S., Rodriguez A.L., Carlson K.E., Sun J., Katzenellenbogen B.S., Katzenellenbogen J.A. J. Med. Chem. 44:2001;3838-3848.
13. Brown C.D., Chong J.M., Shen L. Tetrahedron. 55:1999;14233-14242.
14. Francesconi I., Patel A., Boykin D.W. Synthesis. 1999;61-63.
15. Balaban, A. T.; Dinculescu, A.; Dorofeenki, G. N.; Fischer, G. W.; Koblik, A. V.; Mezheritskii, V. V.; Schroth, W. In Advances in Heterocyclic Chemistry. Supplement 2. Pyrylium Salts: Syntheses, Reactions, and Physical Properties; Katritzky, A. R., Ed.; Academic Press: New York, 1982; Chapter 3.
16. Lombard R., Stephan J.P. Bull. Soc. Chim. Fr. 1958;1458-1462.
17. Martiny M., Steckhan E., Esch T. Chem. Ber. 126:1993;1671-1682.
18. Buchardt O., Pedersen C.L., Svanholm U., Duffield A.M., Balaban A.T. Acta Chem. Scand. 23:1969;3125-3138.
19. Gassman P.G., Lumb J.T., Zalar F.V. J. Am. Chem. Soc. 89:1967;946-952.
20. Gilday J.P., Paquette L.A. Org. Prep. Proceed. Int. 22:1990;167-201.
21. Compound 14 was isolated and characterized fully, including X-ray crystallography (see supplementary material for more information).