Metallation reactions. XXXVI. A study on the metallation of (methylthio)- and (methylsulfonyl)thiophenes

Journal of Heterocyclic Chemistry

Volumn 44, Issue 3, 2007, Pages 609-615

  Fattuoni, Claudia ^a   Usai, Michele ^a   Cabiddu, Maria G ^a   Cadoni, Enzo ^a   De Montis, Stefania ^a   Sotgiu, Francesca ^a   Cabiddu, Salvatore ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 (METHYLSULFONYL)THIOPHENE; 2 (METHYLTHIO)THIOPHENE; 3 (METHYLSULFONYL)THIOPHENE; 3 (METHYLTHIO)THIOPHENE; LITHIUM DERIVATIVE; ORGANOLITHIUM COMPOUND; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DEGRADATION; METALLATION; REACTION ANALYSIS; SYNTHESIS;

EID: 38949171497     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570440316     Document Type: Article

References (33)

1. Hrib, N. J.; Jurcak, J. G.; Bregna, D. E.; Dunn, R. W.; Geyer, H. M.; Hartman, H. B.; Roehr, J. E.; Rogers, K. L.; Rush, D. K.; Szczepanik, A. M.; Szewerak, M. R.; Wilmot, C. A.; Conway, P. G. J. Med. Chem. 1992, 35, 2712-2715 and references cited therein.
2. Connor, D. T.; Cetenko, W. A.; Mullican, M. D.; Sorenson, R. J.; Unangst, P.; Weikert, R. J.; Adolphson, R. L.; Kennedy, J. A.; Thueson, D. O.; Wright, C.; Conroy, M. C. J. Med. Chem. 1992, 35, 958-965 and references cited therein.
3. Ahlheim, M.; Barzoukas, M.; Bedworth, P. V.; Blanchard-Desce, M.; Fort, A.; Hu, Z. Y.; Marder, S. R.; Perry, J. W.; Runser, C.; Staehelin, M.; Zysset, B. Science (Washington D.C.) 1996, 271, 335-337.
4. Benincori, T.; Gladiali, S.; Rizzo, S.; Sannicolò, F. J. Org. Chem. 2001, 66, 5940-5942.
5. Mandal, S. S.; Samanta, S. S.; Deb, C.; De, A. J. Chem. Soc., Perkin Trans. 1 1998, 2559-2562.
6. Mukherjee, C.; Kamila, S.; De, A. Tetrahedron 2003, 59, 4767-4774.
7. Mohamadi, F.; Spees, M. M.; Grindey, G. B. J. Med. Chem. 1992, 35, 3012-3016.
8. Snieckus, V. Chem. Rev. 1990, 90, 879-933 and references cited therein.
9. Clayden, J. In The Chemistry of Organolithium Compounds; Rappoport, Z., Ed.; Patai Series; John Wiley & Sons: Chichester, 2004; pp 495-646.
10. Brandsma, L.; Verkruijsse, H. In Preparative Polar Organometallic Chemistry; Springer-Verlag: Berlin, 1987; Vol. 1, pp 115-184.
11. Clayden, J. In Organolithium: selectivity for synthesis; Tetrahedron organic chemistry series 23; Pergamon: Amsterdam, 2002.
12. Cabiddu, S.; Floris, C.; Melis, S. Tetrahedron Lett. 1986, 27, 4625-4628.
13. Cabiddu, S.; Fattuoni, C.; Floris, C.; Gelli, G.; Melis, S. J. Organometal. Chem. 1992, 441, 197-202.
14. Cabiddu, S.; Fattuoni, C.; Floris, C.; Gelli, G.; Melis, S. Tetrahedron 1993, 49, 4965-4974.
15. Bongini, A.; Savoia, D.; Umani-Ronchi, A. J. Organometal. Chem. 1976, 112, 1-8.
16. Melis, S.; Piras, P. P.; Plumitallo, A. Rend. Sem. Fac. Sci. Univ. Cagliari 1977, 47, 19-24.
17. Cabiddu, M. G.; Cabiddu, S.; Fattuoni, C.; Floris, C.; Gelli, G.; Melis, S. Phosphorus, Sulfur, Silicon 1992, 70, 139-143.
18. Stoyanovich, F. M.; Karpenko, R. G.; Gorushkina, G. I.; Gold'farb, Ya. L. Tetrahedron 1972, 28, 5017-5023.
19. Stoyanovich, F. M.; Fedorov, B. P. Angew. Chem. Int. Ed. Engl. 1966, 5, 127.
20. Schlosser, M. In Modern Synthetic Methods; Scheffold, R., Ed.; Verlag HCA: Basel, and VCH: Weinheim, 1992; Vol. 6, pp 227-271.
21. Mordini, A. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; Jai Press: Greenwich, CT, 1992; Vol. 1, pp 1-45.
22. Gol'dfarb, Ya. L.; Kalik, M. A.; Kirmalova, M. L. Zhur. Obshchei Khim. 1959, 29, 3631-3636.
23. Barbarella, G.; Zambianchi, M.; Ventola, A.; Fabiano, E.; Della Sala, F.; Gigli, G.; Anni, M.; Bolognesi, A.; Polito, L.; Naldi, M.; Capobianco, M. Bioconjugate Chem. 2006, 17, 58-67.
24. Noack, A.; Schroder, A.; Hartmann, H. Dyes and Pigments 2002, 57, 131-147.
25. Gronowitz, S. Ark. Kemi 1958, 13, 269-278.
26. Taylor, E. C.; Vogel, D. E. J. Org. Chem. 1985, 50, 1002-1004 and references cited therein.
27. Karlsson, J. O.; Svensson, A.; Gronowitz, S. J. Org. Chem. 1984, 49, 2018-2020.
28. Belley, M.; Douida, Z.; Mancuso, J.; De Vleeschauwer, M. Synlett. 2005, 247-250 and references cited therein.
29. Duhamel, L.; Plaquevent, J. C. J. Org. Chem. 1979, 44, 3404-3405.
30. Cymerman-Craig, J.; Loder, J. W. J. Chem. Soc. 1954, 237-242.
31. Grafing, R.; Brandsma, L. Tec. Trav. Chim. Pays-Bas 1976, 95, 264-266.
32. Gol'dfarb, Ya. L.; Pokhil, G. P.; Belen'kii,L. I. J. Gen. Chem. USSR 1967, 37, 2541-2546.
33. Cederlund, B.; Lantz, R.; Hornfeldt, A.-B.; Thorstad, O.; Undheim, K. Acta Chem. Scand. 1977, B 31, 198-202.