Atropisomers of 1-(acyl or aroyl)-2-naphthylindolines. Isolation, X-ray crystal structure and conformational analysis

Chemical and Pharmaceutical Bulletin

Volumn 51, Issue 6, 2003, Pages 688-696

  Ito, Fumikazu ^a   Moriguchi, Tetsuya ^a   Yoshitake, Yasuyuki ^a   Eto, Masashi ^a,b   Yahara, Shoji ^a   Harano, Kazunobu ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

^b TOKAI UNIVERSITY   (Japan)

Author keywords

1 aroyl 2 aryl 3,3 dimethylindoline; Conformational analysis; Crystal packing; Diastereomeric atropisomer; NMR; X ray analysis

Indexed keywords

NAPHTHYL GROUP;

ARTICLE; CHEMICAL BOND; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUBSTITUTION REACTION; X RAY ANALYSIS;

EID: 27944491127     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.51.688     Document Type: Article

References (39)

1. Oki M., Angew. Chem., 88, 67-74 (1976).
2. Oki M., "Topics in Stereochemistry," Vol. 14, ed. by Allinger N. L., Eliel E. L., Wilen S. H., John Wiley & Sons Inc., New York, 1983, pp. 47-79.
3. Oki M., Acc. Chem. Res., 23, 351-356 (1990).
4. Randall W. C., Anderson P. S., Cresson E. L., Hunt C. A., Lyon T. F., Rittle K. E., Remy D. C., Springer J. P., Hirshfield J. M., Hoogsteen K., Williams M., Risley E. A., Tataro J. A., J. Med. Chem., 22, 1222-1230 (1979).
5. Cozzi F., Cinquini M., Annunziata R., Dwyer T., Siegel J. S., J. Am. Chem. Soc., 114, 5729-5733 (1992).
6. Cozzi F., Cinquini M., Annunziata R., Siegel J. S., J. Am. Chem. Soc., 115, 5330-5331 (1993), and references cited therein.
7. Harano K., Yasuda M., Ida Y., Komori T., Taguchi T., Cryst. Struc. Commun., 10, 165-171 (1981).
8. Eto M., Harano K., Hisano T., Kitamura T., J. Heterocycl. Chem., 29, 311-315 (1992).
9. Kitamura T., Harano K., Hisano T., Chem. Pharm. Bull., 40, 2255-2261 (1992).
10. Eto M., Ito F., Kitamura T., Harano K., Heterocycles, 38, 2159-2163 (1994).
11. Eto M., Ito F., Kitamura T., Harano K., Heterocycles, 43, 1159-1163 (1996).
12. Watanabe A., Moriguchi M., Ito F., Yoshitake Y., Eto M., Harano K., Heterocycles, 53, 1-6 (2000).
13. SAPI91: Fan Hai-Fu (1991). Structure Analysis Programs with Intelligent Control, Rigaku Corporation, Tokyo, Japan.
14. Johnson C. K., ORTEP, Report ORNL-3794, Ork Ridge National Laboratory, Oak Ridge, TN, 1965.
15. Allen F. H., Kennard O., Watson D. G., Brammer L., Orpen A. G., Taylor R., J. Chem. Soc., Perkin Trans. 2, 1987, S1-S19 (1987).
16. 18)
17. 1=0.080.
18. Taylor R., Kennard O., J. Am. Chem. Soc., 104, 5063-5070 (1982).
19. Desiraju G. R., Acc. Chem. Res., 24, 290-296 (1991).
20. Steiner T., Kanters J. A., Kroon J., Chem. Commun., 1996, 1277-1278 (1996).
21. Nishio M., Hirota M., Tetrahedron, 45, 7201-7245 (1989).
22. Hunter C. A., Sanders J. K. M., J. Am. Chem. Soc., 112, 5525-5534 (1990).
23. Steiner T., Starikov E. B., Amada A. M., Texia-Dias J. J. C., J. Chem. Soc., Perkin Trans. 2, 1995, 1321-1326 (1995).
24. Boyd D. R., Evans T. A., Jennings W. B., Malone J. F., O'Sullivan W., Smith A., J. Chem. Soc., Chem. Commun., 1996, 2269-2270 (1996).
25. Nishio M., Hirota M., Umezawa Y., "The CH/π interaction; Evidence Nature and Consequences," Wiley, New York, 1998.
26. Stewart J. J. P., J. Am. Chem. Soc., 107, 3902-3909 (1985).
27. AM1 calculations were run through the CS Chem Pro interface using MOPAC97 on a Power Macintosh G3 computer.
28. AM1 method is suitable for the structure optimization of atropisomers involving amide groups.
29. The AM1-calculated heats of formation (kcal/mol) based on the four frozen conformations are as follows; anti-syn 31.940, syn-anti 30.387, anti-anti 31.906, syn-syn 30.405. The calculations could not reproduce the relative stability among them.
30. "Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry," 2nd ed., by Jackmann L. M., Sternhell S., Inc., 1969, pp. 72-77.
31. Fukui K., "Kagaku Hanno to Densi no Kido (Chemical Reactions and Electron Orbitals)," Maruzen, Tokyo, 1976.
32. Fleming I., "Frontier Orbitals and Organic Chemical Reactions," Wiley, London, 1976.
33. Sustmann first applied a FMO concept to reactivity in 1.3-dipolar reactions and Diels-Alder (DA) reactions and classified these reactions into three types of cycloadditions according to the relative positions of the frontier orbitals of the reagents. In the normal DA reaction, the interactions LUMO-dienophile and HOMO-diene are the dominant stabilizing factor. For the inverse type reaction the predominant interactions become HOMO-dienophile and LUMO-diene. A third type of orbital arrangement for a DA reaction might be called neutral. The HOMO-LUMO separations are similar, therefore, electron attraction and release should increase the reactivity.
34. The AM1 FMO energy levels are as follows: 2-naphthol LUMO -0.35 eV, HOMO -8.64 eV; 3-nitrobenzoic acid LUMO -1.46 eV; HOMO -10.97 eV; 4-nitrobenzoic acid LUMO -1.73 eV, HOMO -10.90 eV.
35. Brunner K., Monatsh. Chem., 16, 849 (1895).
36. Luechs H., Schlotzer A., Ber., 67, 1572-1576 (1934).
37. see also ref. 10 and references cited therein.
38. Cromer D. T., Abd Waber J. T., "International Tables for X-ray Crystallography," Vol. IV, The Kynoch Press, Birmingham, England, 1974, Table 2.2A.
39. Crystal Structure Analysis Package, Molecular Structure Corporation (1985 & 1992).