Synthesis of novel benzoxazocino quinoliniums and quinolones under PTC conditions and their application in Suzuki cross coupling reaction for the construction of polynuclear heteroaromatics

Tetrahedron

Volumn 65, Issue 34, 2009, Pages 6941-6949

  Sahu, Krishnendu B ^a   Hazra, Abhijit ^a   Paira, Priyankar ^a   Saha, Pritam ^a   Naskar, Subhendu ^a   Paira, Rupankar ^a   Banerjee, Sukdeb ^a   Sahu, Niranjan P ^a   Mondal, Nirup B ^a   Luger, Peter ^b   Weber, Manuela ^b  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOXAZOCINOQUINOLINIUM DERIVATIVE; HETEROCYCLIC STEROID; QUINOLINE DERIVATIVE; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CRYSTAL STRUCTURE; MELTING POINT; MICROWAVE ASSISTED SUZUKI CROSS COUPLING REACTION; MICROWAVE RADIATION; NONHUMAN; PHASE TRANSITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION; SUZUKI REACTION; SYNTHESIS;

EID: 67650531423     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.061     Document Type: Article

References (31)

1. Czarnik A.W. Acc. Chem. Res. 29 (1996) 112-113
2. Fagnoni M. Heterocycles 60 (2003) 1921-1958
3. Hajos G., Riedl Z., and Kollenz G. Eur. J. Org. Chem. (2001) 3405-3414
4. Majumdar K.C., Basu P.K., and Mukhopadhyay P.P. Tetrahedron 60 (2004) 6239-6278
5. Barchechath S.D., Tawatao R.I., Corr M., Carson D.A., and Cottam H.B. Bioorg. Med. Chem. Lett. 15 (2005) 1785-1788
6. Brana M.F., Cacho M., Gradillas A., Pascual-teresa B., and Ramos A. Curr. Pharm. Des. 7 (2001) 1745-1780
7. Martinez R., and Chacon-Garcia L. Curr. Med. Chem. 12 (2005) 127-151
8. Nicolaou K.C., Huang X., Giuseppone N., Rao P.B., Bella M., Reddy M.V., and Snyder S.A. Angew. Chem., Int. Ed. 40 (2001) 4705-4709
9. Ollis W.D., Stanforthand S.P., and Ramsden C.A. Tetrahedron 41 (1985) 2239-2329
10. Maruoka K. Org. Process Res. Dev. 12 (2008) 679-697
11. Dutta R., Mandal D., Panda N., Mondal N.B., Banerjee S., Kumer S., Weber M., Lugar P., and Sahu N.P. Tetrahedron Lett. 45 (2004) 9361-9364
12. Paira P., Hazra H., Sahu K.B., Banerjee S., Mondal N.B., Sahu N.P., Weber M., and Lugar P. Tetrahedron 64 (2008) 4026-4036
13. Alfonsi P., Adam F., Passarel A., Guiqnard B., Sessler D.I., and Chauvin M. Anesthesiology 100 (2004) 37-43
14. Rosamilia A.E., Mayes P.A., Papadopoulos R., Campi E.M., Roy Jackson W., Rash L., and Jarrott B. Aust. J. Chem. 55 (2002) 577-585
15. Heel R.C., Broqden R.N., Pakes G.E., Speight T.M., and Avery G.S. Drugs 19 (1980) 249-267
16. Wang R.I., and Waite E.M. J. Chin. Pharmacol. 19 (1979) 395-402
17. Cohen A., and Hernandez C.M. J. Int. Med. Res. 4 (1976) 138-143
18. For recent reviews, see:
19. Hassan J., Sévignon M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359-1470
20. Suzuki A. J. Organomet. Chem. 576 (1999) 147-168
21. Kertesz M., Choi C.H., and Yang S. Chem. Rev. 105 (2005) 3448-3481
22. Capdeville R., Buchdunger E., Zimmermann J., and Matter A. Nat. Rev. Drug Discovery 1 (2002) 493-502
23. Tomori H., Fox J.M., and Buchwald S.L. J. Org. Chem. 65 (2000) 5334-5341
24. Lightowler S., and Hirz M. Chem. Mater. 17 (2005) 5538-5549
25. Jean-Gérard L., Pauvert M., Collet S., Guingan A., and Evain M. Tetrahedron 63 (2007) 11250-11259
26. Lidström P., Tierney J., Wathey B., and Westman J. Tetrahedron 57 (2001) 9225-9283
27. Siemens (2004). SMART, SAINT, XPREP and SADABS. Area Detector Control and Integration Software. Bruker Analytical X-ray Instruments Inc., Madison, wisconsin, USA.
28. SIR 2002:. Burla M.C., Camalli M., Carrozzini B., Cascarano G.L., Giacovazzo C., Polidori G., and Spagna R. J. Appl. Crystallogr. 36 (2003) 1103
29. Sheldrick G.M. Acta Crystallogr. A64 (2008) 112-122
30. Burnett M.N., and Johnson C.K. ORTEP III, Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustration (1996), Oak Ridge National Laboratory Report ORNL-6895, Oak Ridge, Tennessee, TN, USA
31. Keller E., and Pierrard J.S. Schakal99. A Fortran Program for the Graphical Representation of Molecular and Crystallographic Models (1999), Univ. Freiburg, Germany