Studies on rotational barriers of N-C axially chiral compounds: Increase in the rotational barrier by aromatization

Tetrahedron Letters

Volumn 53, Issue 33, 2012, Pages 4332-4336

  Suzumura, Naomi ^a   Kageyama, Masato ^a   Kamimura, Daichi ^a   Inagaki, Takahiro ^a   Dobashi, Yasuo ^b   Hasegawa, Hiroshi ^b   Fukaya, Haruhiko ^b   Kitagawa, Osamu ^a  

^a SHIBAURA INSTITUTE OF TECHNOLOGY   (Japan)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Aromatization; Axially chiral; Quinazolinone; Quinolinone; Rotational barrier

Indexed keywords

CARBON; NITROGEN; QUINAZOLINE DERIVATIVE; QUINOLINE DERIVATIVE;

AROMATIZATION; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; PHASE TRANSITION; ROTATION;

EID: 84864059247     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.06.007     Document Type: Article

References (42)

1. Typical examples of atropisomeric compounds having an N-C chiral axis: L.H. Bock, and R. Adams J. Am. Chem. Soc. 53 1931 374
2. C. Kashima, and A. Katoh J. Chem. Soc., Perkin Trans. 1 1980 1599
3. A. Mannschreck, H. Koller, G. Stühler, M.A. Davis, and J. Traber Eur. J. Med. Chem. Chim. Ther. 19 1984 381
4. C. Roussel, M. Adjimi, A. Chemlal, and A. Djafri J. Org. Chem. 53 1988 5076
5. T. Kawamoto, M. Tomishima, F. Yoneda, and J. Hayami Tetrahedron Lett. 33 1992 3169
6. X. Dai, A. Wong, and S.C. Virgil J. Org. Chem. 63 1998 2597
7. D.P. Curran, W. Liu, and C.H. Chen J. Am. Chem. Soc. 121 1999 11012
8. T. Hata, H. Koide, N. Taniguchi, and M. Uemura Org. Lett. 2 2000 1907
9. K.D. Shimizu, H.O. Freyer, and R.D. Adams Tetrahedron Lett. 41 2000 5431
10. Tetrahedron Symposium-in-print on Axially Chiral Amides (Atropisomerism), J. Clayden, (Ed.), Tetrahedron, 2004, 60, 4325-4558.
11. T. Tokitoh, T. Kobayashi, E. Nakada, T. Inoue, S. Yokoshima, H. Takahashi, and H. Natsugari Heterocycles 70 2006 93
12. K. Kamikawa, S. Kinoshita, M. Furusyo, S. Takemoto, H. Matsuzaka, and M. Uemura J. Org. Chem. 72 2007 3394
13. E.M. Yilmaz, and I. Dogan Tetrahedron Asymmetry 19 2008 2184
14. Typical papers on atropisomeric ortho-tert-butylanilides: D.P. Curran, H. Qi, S.J. Geib, and N.C. DeMello J. Am. Chem. Soc. 116 1994 3131
15. K. Kishikawa, I. Tsuru, S. Kohomoto, M. Yamamoto, and K. Yamada Chem. Lett. 1994 1605
16. O. Kitagawa, H. Izawa, K. Sato, A. Dobashi, T. Taguchi, and M. Shiro J. Org. Chem. 63 1998 2634
17. A.D. Hughes, D.A. Price, and N.S. Simpkins J. Chem. Soc., Perkin Trans. 1 1999 1295
18. T. Bach, J. Schröder, and K. Harms Tetrahedron Lett. 40 1999 9003
19. D.P. Curran, S. Geib, and N. Demello Tetrahedron 55 1999 5681
20. K. Kondo, T. Iida, H. Fujita, T. Suzuki, K. Yamaguchi, and Y. Murakami Tetrahedron 56 2000 8883
21. S. Dantale, V. Reboul, P. Metzner, and C. Philouze Chem. Eur. J. 8 2002 632
22. D.J. Bennett, A.J. Blake, P.A. Cooke, R.A. Godfrey, P.L. Pickering, N.S. Simpkins, M.D. Walker, and C. Wilson Tetrahedron 60 2004 4491
23. In addition to III-VI, other stable N-C axially chiral aromatic heterocycles (quinolin-2-one and pyridin-2-one) having an N-(ortho-methyl)phenyl group have also been reported. M. Mintas, V. Mihaljevic, H. Koller, D. Schuster, and A. Mannschreck J. Chem. Perkin Trans. 2 1990 619
24. M. Sakamoto, N. Utsumi, M. Ando, M. Seki, T. Mino, T. Fujita, A. Katoh, T. Nishino, and C. Kashima Angew. Chem., Int. Ed. 42 2003 4360
25. K. Tanaka, Y. Takahashi, T. Suda, and M. Hirano Synlett 2008 1724 See also Ref. 1l.
26. 1d having a five-membered ring structure cannot be rationalized on the basis of such bond angle. Kitagawa, O.; Fujita, M.; Kohriyama, M.; Hasegawa, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 8539.
27. Reviews on medicinal drugs having atropisomeric structure J. Clayden, W.J. Moran, P.J. Edwards, and S.R. LaPlante Angew. Chem., Int. Ed. 48 2009 6398
28. S.R. LaPlante, L.D. Fader, K.R. Fandrick, D.R. Fandrick, O. Hucke, R. Kemper, S.P.F. Miller, and P.J. Edwards J. Med. Chem. 54 2011 7005
29. O. Kitagawa, H. Hirotaka, A. Dobashi, T. Taguchi, and M. Shiro Tetrahedron Lett. 38 1997 4447
30. O. Kitagawa, and T. Taguchi Yuki Gosei Kagaku Kyokaishi 59 2001 680
31. M. Takahashi, and O. Kitagawa Yuki Gosei Kagaku Kyokaishi 69 2011 985
32. N. Ototake, Y. Morimoto, A. Mokuya, H. Fukaya, Y. Shida, and O. Kitagawa Chem. Eur. J. 16 2010 6752 and references cited therein
33. O. Kitagawa, M. Takahashi, M. Yoshikawa, and T. Taguchi J. Am. Chem. Soc. 127 2005 3676
34. O. Kitagawa, M. Yoshikawa, H. Tanabe, T. Morita, M. Takahashi, Y. Dobashi, and T. Taguchi J. Am. Chem. Soc. 128 2006 12923
35. Catalytic enantioselective synthesis of N-C axially chiral compounds by other groups S. Brandes, M. Bella, A. Kjoersgaard, and K.A. Jorgensen Angew. Chem., Int. Ed. 45 2006 1147
36. K. Tanaka, K. Takeishi, and K. Noguchi J. Am. Chem. Soc. 128 2006 4586
37. W. Duan, Y. Imazaki, R. Shintani, and T. Hayashi Tetrahedron 63 2007 8529
38. J. Oppenheimer, R.P. Hsung, R. Figueroa, and W.L. Johnson Org. Lett. 9 2007 3969
39. J. Clayden, and H. Turner Tetrahedron Lett. 50 2009 3216
40. G. Onodera, M. Suto, and R. Takeuchi J. Org. Chem. 77 2012 908
41. S. Shirakawa, K. Liu, and K. Maruoka J. Am. Chem. Soc. 134 2012 916
42. DFT calculations at the level of B3LYP1/6-31G(d) were performed by Firefly (PC GAMESS) quantum chemical package (version 7.1.G, Alex A. Granovsky, Firefly version 7.1.G, www http://classic.chem.msu.su/gran/firefly/index.html). All structures were fully optimized and then subjected to the frequency analysis. For the ground state, the absence of the imaginary frequency was confirmed in every case. Transition states relevant to the rotational barrier were identified by the following two criteria: (1) The frequency analysis gave only one imaginary frequency. (2) The exhaustive IRC calculations provided one pair of enantiomeric atropisomers. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A.; J. Comput. Chem. 1993, 14, 1347.