Synthesis of new thieno[3,2-b]pyridine derivatives by palladium-catalyzed couplings and intramolecular cyclizations

Tetrahedron Letters

Volumn 51, Issue 2, 2010, Pages 281-283

  Calhelha, Ricardo C ^a   Queiroz, Maria João R P ^a  

^a UNIVERSITY OF MINHO   (Portugal)

Author keywords

Intramolecular cyclization; Palladium catalyzed couplings; Tetracyclic compounds; Thieno 3,2 b pyridines

Indexed keywords

AROMATIC AMINE; CARBON; METHYL 3 AMINO 6 BROMOTHIENO[3,2 B]PYRIDINE 2 CARBOXYLATE; METHYL 3 AMINOTHIENO[3,2 B]PYRIDINE 2 CARBOXYLATE DERIVATIVE; NITRILE; NITROBENZENE DERIVATIVE; NITROGEN; PALLADIUM; PYRIDINE DERIVATIVE; THIOGLYCOLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CATALYSIS; CHEMICAL BOND; CYCLIZATION; DRUG SYNTHESIS; SONOGASHIRA REACTION; SUZUKI REACTION;

EID: 71049172883     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.10.138     Document Type: Article

References (22)

1. Munchhof M.J., Beebe J.S., Casavant J.M., Cooper B.A., Doty J.L., Hidgon R.C., Hillerman S.M., Doderstrom C.I., Knauth E.A., Marx M.A., Rossi A.M.K., Sobolov S.B., and Sun J. Bioorg. Med. Chem. Lett. 14 (2004) 21-24
2. Claridge S., Raeppel F., Granger M.-C., Bernstein N., Saavedra O., Zhan L., Llewellyn D., Wahhab A., Deziel R., Rahil J., Beaulieu N., Nguyen H., Dupont I., Barsalou A., Beaulieu C., Chute I., Gravel S., Robert M.-F., Lefebvre S., Dubay M., Pascal R., Gillespie J., Jin Z., Wang J., Besterman J.M., MacLeod A.R., and Vaisburg A. Bioorg. Med. Chem. Lett. 18 (2008) 2793-2798
3. Heyman H.R., Frey R.R., Bousquet P.F., Cunha G.A., Moskey M.D., Ahmed A.A., Soni N.B., Marcotte P.A., Pease L.J., Glaser K.B., Yates M., Bouska J.J., Albert D.H., Black-Schaefer C.L., Dandliker P.J., Stewart K.D., Rafferty P., Davidsen S.K., Michaelides M.R., and Curtin M.L. Bioorg. Med. Chem. Lett. 17 (2007) 1246-1249
4. Yin L., Shan W., Jia X., Li X., and Chan A.S.C. J. Organomet. Chem. 694 (2009) 2092-2095
5. Yang J., Hua W.-Y., Wang F.-X., Wang Z.-Y., and Wang X. Biorg. Med. Chem. 12 (2004) 6547-6557
6. Comoy C., Banaskak E., and Fort Y. Tetrahedron 62 (2006) 6036-6041
7. Queiroz M.-J.R.P., Calhelha R.C., and Kirsch G. Tetrahedron 63 (2007) 13000-13005 and references cited therein
8. Dunn A.D., and Norrie R. J. Heterocycl. Chem. 24 (1987) 85-89
9. 2S 287.9391, found 287.9389.
10. For reviews on C-N Buchwald-Hartwig coupling see:. Hartwig J.F. Synlett (1997) 329-340
11. Hartwig J.F. Angew. Chem., Int. Ed. 37 (1998) 2046-2067
12. Wolfe J.P., Wagaw S., Marcoux J.-F., and Buchwald S.L. Acc. Chem. Res. 31 (1998) 805-818
13. Yang B.H., and Buchwald S.L. J. Organomet. Chem. 576 (1999) 125-146
14. Muci A.R., and Buchwald S.L. Top. Curr. Chem. 219 (2002) 131-209
15. Dai Y., Guo Y., Frey R.R., Ji Z., Curtin M.L., Ahmed A.A., Albert D.H., Arnold L., Arries S.S., Barlozzari T., Bauch J.L., Bouska J.J., Bousquet P.F., Cunha G.A., Glaser K.B., Guo J., Li J., Marcotte P.A., Marsh K.C., Moskey M.D., Pease L.J., Stewart K.D., Stoll V.S., Tapang P., Wishart N., Davidsen S.K., and Michaelides M.R. J. Med. Chem. 48 (2005) 6066-6083
16. Bunce R.A., and Schammerhorn J.E. J. Heterocycl. Chem. 43 (2006) 1031-1035
17. For a recent review on the Suzuki reaction see:. Alonso F., Belestskaya I.P., and Yus M. Tetrahedron 64 (2008) 3047-3101
18. Murata M., Oyama T., Watanabe S., and Masuda Y. J. Org. Chem. 65 (2000) 164-168
19. For a recent review on organotrifluoroborates see:. Stefani H.A., Cella R., and Vieira A.S. Tetrahedron 63 (2007) 3623-3658
20. For a recent review on the Sonogashira reaction see:. Chincilla R., and Nájera C. Chem. Rev. 107 (2007) 874-922
21. 2S 383.0728, found 383.0729.
22. Castanheira E.M.S., Pinto A.M.R., and Queiroz M.-J.R.P. J. Fluorescence 16 (2006) 251-257