Synthesis of polycyclic and 4,5-diacylthiophene-2-carboxylates via intramolecular Friedel-Crafts alkylations and unusual autooxidative fragmentation of the derivatives obtained from the samarium diiodide-promoted coupling reactions of thiophene-2-carboxylate with carbonyl compounds

Tetrahedron

Volumn 63, Issue 6, 2007, Pages 1421-1428

  Yang, Shyh Ming ^a   Fang, Jim Min ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

Autooxidation; Coupling reaction; Fragmentation; Samarium diiodide; Thieno 2,3 d pyridazine; Thiophene

Indexed keywords

ACETOPHENONE DERIVATIVE; ALDEHYDE; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; PYRIDAZINE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL PROCEDURES; CHEMICAL REACTION; CONJUGATION; FRAGMENTATION REACTION; FRIEDEL CRAFTS REACTION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 33845713114     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.11.080     Document Type: Article

References (34)

1. Roncali J. Chem. Rev. 92 (1992) 711
2. Roncali J. Chem. Rev. 97 (1997) 173
3. Miller L.L., and Mann K.R. Acc. Chem. Res. 29 (1996) 417
4. Larsen J., and Bechgaard K. Acta Chem. Scand. 50 (1996) 71
5. Müller M., Mauermann-Dull H., Wagner M., Enkelmann V., and Müllen K. Angew. Chem., Int. Ed. Engl. 34 (1995) 1583
6. Tsuji K., Nakamura K., Ogino T., Konishi N., Tojo T., Ochi T., Seki N., and Matsuo M. Chem. Pharm. Bull. 46 (1998) 279
7. Becker F.F., Mukhopadhyay C., Hackfeld L., Banik I., and Banik B.K. Bioorg. Med. Chem. 8 (2000) 2693
8. For reviews on the synthetic methods of thiophene derivatives, see:
9. Campaigne E. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 4 (1984), Elsevier, Oxford 863-934
10. Nakayama J. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 2 (1996), Elsevier, Oxford 607-677
11. Kozmík V., and Paleèek J. Collect. Czech. Chem. Commun. 57 (1992) 1483
12. Sniekus V. Chem. Rev. 90 (1990) 879
13. MacDowell D.W.H., and Ballas F.L. J. Org. Chem. 42 (1977) 3717
14. Beleńkii L.I., Gromova G.P., Kolotaev A.V., and Krayushkin M.M. Chem. Heterocycl. Compd. (Engl. Transl.) 36 (2000) 256
15. Pirson P., Schonne A., and Christiaens L. Bull. Soc. Chim. Belg. 79 (1970) 575
16. Yang S.-M., and Fang J.-M. Tetrahedron Lett. 38 (1997) 1589
17. Yang S.-M., Nandy S.K., Selvakumar A.R., and Fang J.-M. Org. Lett. 2 (2000) 3719
18. Shie J.-J., Yang S.-M., Chen C.-T., and Fang J.-M. Org. Lett. 4 (2002) 1099
19. Yang S.-M., Shie J.-J., Fang J.-M., Nandy S.K., Chang H.-Y., Lu S.-H., and Wang G. J. Org. Chem. 67 (2002) 5208
20. Babu G., Yu H.-M., Yang S.-M., and Fang J.-M. Bioorg. Med. Chem. Lett. 14 (2004) 1129
21. For biological role of endothelins, see:
22. Yanagisawa M., Kurihara H., Kimura S., Tomobe Y., Kobayashi M., Mitsui Y., Yazaki Y., Goto K., and Masaki T. Nature 332 (1988) 311
23. Doherty A.M. J. Med. Chem. 35 (1992) 1493
24. Schiffrin E.L., and Touyz R.M. J. Cardiovasc. Pharmacol. 32 (1998) 2
25. For review on endothelin antagonists, see:. Elliott J.D., Lago M.A., and Peishoff C.E. In: Ruffolo R.R. (Ed). Endothelin Receptors: from the Gene to the Human (1995), CRC, Boca Raton, FL 79
26. Doherty A.M. Drug Discov. Today 1 (1996) 60
27. Webb M.L., and Meek T.D. Med. Res. Rev. 17 (1997) 17
28. Liu G. Annu. Rep. Med. Chem. 35 (2000) 73
29. Boigegrain, R.; Maffrand, J. P. Thieno[2,3-d]pyridazin-4-ones and thieno[2,3-d]pyridazin-7-ones and their therapeutic use. Fr. Demande 1981, p 22;
30. Boigegrain, R.; Maffrand, J. P. Thieno[2,3-d]pyridazines and their therapeutic application. Fr. Demande 1981, p 18.
31. Hood, H. E. Process for producing phenol by acid-catalyzed cleavage of cumene hydroperoxide. U.S. Patent 1994, p 22;
32. Lewandowski G., and Milchert E. Przem. Chem. 81 (2002) 103
33. Takai T. Shokubai 45 (2003) 354
34. Levin M.E., Gonzales N.O., Zimmerman L.W., and Yang J. J. Hazard. Mater. 130 (2006) 88