De novo synthesis of thiophenes on a polymeric support

Tetrahedron Letters

Volumn 48, Issue 20, 2007, Pages 3535-3538

  Traversone, Antonio ^a   Brill, Wolfgang K D ^a  

^a Nerviano Medical Sciences Srl ^*  (Italy)

Author keywords

Arils; Chlorotrityl resin; Hinsberg reaction; Intramolecular Wittig reaction; Knoevenagel; Thiophenes

Indexed keywords

THIOGLYCOLIC ACID; THIOPHENE DERIVATIVE;

ARTICLE; KNOEVENAGEL CONDENSATION; OLEFINATION; REACTION ANALYSIS; SYNTHESIS; WITTIG REACTION;

EID: 34247159571     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.111     Document Type: Article

References (19)

1. Sperry J.B., and Wright D.L. Curr. Opin. Drug Discovery Dev. 8 (2005) 723-740
2. Siebert C. Chem. Unserer Zeit 38 (2004) 320-324
3. Alhalasah W., and Holze R. J. Solid State Electrochem. 9 (2005) 836-844
4. Comel A., Sommen G., and Kirsch G. Mini-Rev. Org. Chem. 1 (2004) 367-374
5. Hinsberg O. Ber. Dtsch. Chem. Ges. 45 (1913) 2413-2418
6. Wynberg H., and Kooreman H.J. J. Am. Chem. Soc. 87 (1965) 1739-1742
7. Paranjpe P.P., and Bagavant G. Indian J. Chem. 11 (1973) 313-314
8. Scicinski J.J., Congreve M.S., Jamieson C., Ley S.V., Newman E.S., Vinader V.M., and Carr R.A.E. J. Comb. Chem. 3 (2001) 387-396
9. Bhaskar Reddy D., Muralidhar Reddy M., and Ramana Reddy P.V. Indian J. Chem. 32 B (1993) 1018-1023
10. + Found: 206.0856.
11. Ferguson J., and Marzabadi C. Tetrahedron Lett. 44 (2003) 3573-3577
12. Ranganathan S., and Jayaraman N. J. Chem., Soc., Chem. Commun. 14 (1991) 934-936
13. + Found: 367.0915.
14. ® using 5 mL PP-fritt reactors equipped with a heating block and an orbital shaker. (Mettler-Toledo Bohdan, 562 Bunker Court, Vernon Hills, IL 60610 USA).
15. Schwesinger R. Chimia 39 (1985) 269-272
16. 11 dried down in vacuo, and subjected to analytical HPLC for purity determination. (gradient: 10-90% MeCN-aq 0.1% TFA, 10 min) Products of inferior purity were subjected to preparative mass triggerd HPLC using the same gradient (Table 2).
17. Pyridilic acid rearrangement. Klosa J. J. Prakt. Chem. (Leipzig) 10 (1960) 335-339
18. Furilic acid rearrangement. Pennanen S. Acta. Chem. Scand. 26 (1972) 1280-1281
19. Phosphonium-ylide based thiophene synthesis. Kobayashi T., Ono K., Suda H., Yamashita Y., and Kato H. Bull. Chem. Soc. Jpn. 66 (1993) 2707-2713