Application of quantum chemical calculations of 13C NMR chemical shifts to quinoxaline structure determination

Tetrahedron Letters

Volumn 45, Issue 21, 2004, Pages 4003-4007

  Balandina, Alsu ^a   Mamedov, Vakhid ^a   Franck, Xavier ^b   Figadère, Bruno ^b   Latypov, Shamil ^a  

^a A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; QUINOXALINE DERIVATIVE;

ARTICLE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; QUANTUM CHEMISTRY; RELIABILITY; THEORETICAL MODEL; X RAY DIFFRACTION;

EID: 2342521466     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.182     Document Type: Article

References (36)

1. Gazit A., App H., McMahon G., Chen J., Levitzki A., Bohmer F.D. J. Med. Chem. 39:1996;2170-2177
2. Campiani G., Cappelli A., Nacci V., Anzini M., Vomero S., Hamon M., Cagnotto A., Fracasso C., Uboldi C., Caccia S., Consolo S., Mennini T. J. Med. Chem. 40:1997;3670-3678
3. Jie Jack Li J. Org. Chem. 64:1999;8425-8427
4. Jacobsen E.J., Stelzer L.S., TenBrink R.E., Belonga K.L., Carter D.B., Im H.K., Im W.B., Sethy V.H., Tang A.H., VonVoigtlander P.F., Petke J.D., Zhong W.Z., Mickelson J.W. J. Med. Chem. 42:1999;1123-1144
5. Catarzi D., Colotta V., Varano F., Filacchioni G., Galli A., Costagli C., Carla V. J. Med. Chem. 44:2001;3157-3165
6. Langouet S., Welti D.H., Kerriguy N., Fay L.B., Huynh-Ba T., Markovic J., Guengerich F.B., Guillouzo A., Turesky R.J. Chem. Res. Toxicol. 14:2001;211-221
7. Emsly J.M., Feeney J., Sutcliffe L.H. High Resolution NMR Spectroscopy. 2:1966;127-128
8. Gunther H. NMR Spectroscopy: An Introduction. 1987;John Wiley & Sons, New York
9. Atta-ur-Rahman One and Two Dimensional NMR Spectroscopy. 1989;Elsevier, Amsterdam. p. 579
10. Croasmun W.R., Carlson R.M.K. Two-Dimensional NMR Spectroscopy. 1987;VCH, Weinheim
11. Derome A.E. Modern NMR Techniques for Chemistry Research. 1988;Pergamon
12. Levy G.C. Topics in Carbon-13 NMR Spectroscopy. 1979;Wiley-Interscience, New York
13. Shamma M., Hindenlang D.M. Carbon-13 NMR Shift Assignment of Amines and Alkaloids. 1979;Plenum Press, New York. p. 304
14. Breitmaier E., Voelter W. Carbon-13 NMR Spectroscopy: High Resolution Methods and Applications in Organic Chemistry and Biochemistry. 1987;VCH, Weinheim
15. De Dios A. Progr. Nucl. Magn. Res. Spectrosc. 29:1996;229-278
16. Forsyth D.A., Sebag A.B. J. Am. Chem. Soc. 119:1997;9483-9494
17. Cmoch P., Wiench J.W., Stefaniak L., Sitkowski J. J. Mol. Struct. 477:1999;119-125
18. Cmocha P., Wiencha J.W., Stefaniaka L., Webb G.A. J. Mol. Struct. 510:1999;165-178
19. Havlin R.H., Laws D.D., Bitter H.M.L., Sanders L.K., Sun H., Grimley J.S., Wemmer D.E., Pines A., Oldfield E. J. Am. Chem. Soc. 123:2001;10362-10369
20. Meier M.S., Spielmann H.P., Bergosh R.G., Haddon R.C. J. Am. Chem. Soc. 124:2002;8090-8094
21. Havlin R.H., Le H., Laws D.D., De Dios A., Oldfield E. J. Am. Chem. Soc. 119:1997;11951-11958
22. Gomila R.M., Quinonero D., Rotger C., Garau C., Frontera A., Ballester P., Costa A., Deya P.M. Org. Lett. 4:2002;399-401
23. Rossi P., Harbison G.S. J. Mag. Res. 151:2001;1-8
24. Olah G.A., Burrichter A., Rasul G., Christe K.O., Prakash S. J. Am. Chem. Soc. 119:1997;4345-4352
25. Barfield M., Fagerness P. J. Am. Chem. Soc. 119:1997;8699-8711
26. Sebag A.B., Friel C.J., Hanson R.N., Forsyth D.A. J. Org. Chem. 65:2000;7902-7912
27. Sebag A.B., Forsyth D.A., Plante M.A. J. Org. Chem. 66:2001;7967-7973
28. Lampert H., Mikenda W., Karpfen A., Kalhlig H. J. Phys. Chem. A. 101:1997;9610-9617
29. Rich J.E., Manalo M.N., Dios A.C. J. Phys. Chem. A. 104:2000;5837-5842
30. Alkorta I., Elguero J. Struct. Chem. 14:2003;377-389
31. 13C NMR signals of the compounds were accomplished by 2D HSQC, HMBC, COSY experiments.
32. Mamedov V.A., Levin Ya.A. Khimiya Heterocycl. Soed. (Rus). 7:1996;1005
33. 2 group: ipso (i), ortho (o), meta (m) and para (p). Numbering/assignment of these atoms can be done only after the isomeric structure is established
34. Stott K., Stonehouse J., Keeler J., Hwang T.L., Shaka A.J. J. Am. Chem. Soc. 117:1995;4199-4200
35. Neuhaus D., Williamson M.P. The Nuclear Overhauser Effect in Structural and Conformational Analysis. 1989;VCH, New York
36. Plaza A., Bifulco G., Hamed A.I., Pizza C., Piacente S. Tetrahedron Lett. 44:2003;8553-8558