Synthesis of functionalized triarylmethanes based on a 'FeCl3-catalyzed benzylation/[3+3] cyclocondensation' strategy

Tetrahedron Letters

Volumn 50, Issue 13, 2009, Pages 1490-1492

  Ahmad, Rasheed ^a   Riahi, Abdolmajid ^a,b   Langer, Peter ^a,b  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Arenes; Catalysis; Cyclizations; Regioselectivity; Silyl enol ethers

Indexed keywords

ACETYLACETONE; FERRIC CHLORIDE; METHANE; PENTANE;

ARTICLE; BENZYLATION; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 59649119147     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.079     Document Type: Article

References (34)

1. Bindal R.D., Golab J.T., and Katzenellenbogen J.A. J. Am. Chem. Soc. 112 (1990) 7861
2. Jendralla H., Granzer E., Kerekjarto B.v., Krause R., and Schacht U. J. Med. Chem. 34 (1991) 2962
3. Costantino L., Ferrari A.M., Gamberini M.C., and Rastelli G. Bioorg. Med. Chem. 10 (2002) 3923
4. Al-Qawasmeh R.A., Lee Y., Cao M.-Y., Gu X., Vassilakos A., Wright J.A., and Young A. Bioorg. Med. Chem. Lett. 14 (2004) 347
5. Mibu N., Yokomizo K., Uyeda M., and Sumoto K. Chem. Pharm. Bull. 51 (2003) 1325
6. Schultz T.W., Sinks G.D., and Cronin M.T.D. Environ. Toxicol. 17 (2002) 14
7. Wang P., Kozlowski J., and Cushman M. J. Org. Chem. 57 (1992) 3861
8. Long Y.-Q., Jiang X.-H., Dayam R., Sanchez T., Shoemaker R., Sei S., and Neamati N. J. Med. Chem. 47 (2004) 2561
9. Matulenko M.A., Surber B., Fan L., Kolasa T., Nakane M., Terranova M.A., Uchic M.E., Miller L.N., Chang R., Donnelly-Roberts D.L., and Namovic M.T. Bioorg. Med. Chem. Lett. 14 (2004) 5095
10. Bai L., Masukawa N., Yamaki M., and Takagi S. Phytochemistry 47 (1998) 1637
11. Jin C., Michetich R.G., and Daneshtalab M. Phytochemistry 50 (1999) 505
12. Bindal R.D., and Katzenellenbogen J.A. J. Med. Chem. 31 (1988) 1978
13. Seligmann O., and Wagner H. Tetrahedron 37 (1981) 2601
14. Cushman M., Kanamathareddy S., De Clerq E., Schols D., Goldman M.E., and Bowen J.A. J. Med. Chem. 34 (1991) 337
15. Parmar V.S., Bisht K.S., Jain R., Singh S., and Sharma S.K. Indian J. Chem., Sect. B 35 (1996) 220
16. Jovel I., Mertins K., Kischel J., Zapf A., and Beller M. Angew. Chem. 117 (2005) 3981 Angew. Chem., Int. Ed. 2005, 44, 3913
17. Mertins K., Jovel I., Kischel J., Zapf A., and Beller M. Angew. Chem. 117 (2005) 242 Angew. Chem., Int. Ed. 2005, 44, 238
18. Christoffers J. J. Chem. Soc., Perkin Trans. 1 (1997) 3141
19. Christoffers J. Eur. J. Org. Chem. 7 (1998) 1259
20. Christoffers J., and Oertling H. Tetrahedron 56 (2000) 1339
21. Kischel J., Mertins K., Michalik D., Zapf A., and Beller M. Adv. Synth. Catal. 349 (2007) 865
22. Bisaro F., Prestat G., Vitale M., and Poli G. Synlett (2002) 1823
23. Gullickson G.C., and Lewis D.E. Aust. J. Chem. 56 (2003) 385
24. Yasuda M., Somyo T., and Baba A. Angew. Chem. 118 (2006) 807 Angew. Chem., Int. Ed. 2006, 45, 793
25. Rueping M., Nachtsheim B.J., and Ieawsuwan W. Adv. Synth. Catal. 348 (2006) 1033
26. Yao X., and Li C.J. J. Am. Chem. Soc. 126 (2004) 6884
27. Yao X., and Li C.J. J. Org. Chem. 70 (2005) 5752
28. Motokura K., Fujita N., Mori K., Mizugaki T., Ebitani K., and Kaneda K. Angew. Chem. 118 (2006) 2667 Angew. Chem., Int. Ed. 2006, 45, 2605
29. Chan T.-H., and Brownbridge P. J. Am. Chem. Soc. 102 (1980) 3534
30. Brownbridge P., Chan T.-H., Brook M.A., and Kang G.J. Can. J. Chem. 61 (1983) 688
31. Review of [3+3] cyclizations:. Feist H., and Langer P. Synthesis (2007) 327
32. Review of 1,3-bis(trimethylsilyloxy)-1,3-dienes:. Langer P. Synthesis (2002) 441
33. 4 and the solvents were distilled off. Then, the product was purified by column chromatography (heptanes/ethyl acetate = 1:1).
34. +: 346.156966; found: 346.15635.