Diels-Alder reaction of cyclopentadienone acetal with pyrrole and indole

Bulletin of the Chemical Society of Japan

Volumn 79, Issue 8, 2006, Pages 1288-1292

  Sato, Sota ^a   Fujino, Tomoko ^a   Isobe, Hiroyuki ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE; PYRROLE; REGIOSELECTIVITY;

ELECTRONS; MOLECULAR DYNAMICS; NITROGEN COMPOUNDS; REACTION KINETICS;

AROMATIC COMPOUNDS;

1 METHYLPYRROLE; 1H INDOLE; 1H PYRROLE; 2 CHLORO 1 METHYLPYRROLE; ACETAL DERIVATIVE; CYCLOPENTADIENONE ACETAL; INDOLE DERIVATIVE; POLYCYCLIC AROMATIC COMPOUND; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIELS ALDER REACTION; MOLECULAR INTERACTION; X RAY CRYSTALLOGRAPHY;

EID: 33750633511     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.79.1288     Document Type: Article

References (20)

1. Z. Chen, M. L. Trudell, Chem. Rev. 1996, 96, 1179.
2. R. A. Jones, Pyrroles (The Chemistry of Heterocyclic Compounds), Wiley, New York, 1990.
3. E. Wenkert, P. D. R. Moeller, S. R. Piettre, J. Am. Chem. Soc. 1988, 110, 7188.
4. M.-F. Hsieh, R. K. Peddinti, C.-C. Liao, Tetrahedron Lett. 2001, 42, 5481.
5. J.-H. Li, J. K. Snyder, J. Org. Chem. 1993, 58, 516.
6. R. M. Acheson, J. M. Vernon, J. Chem. Soc. 1961, 457.
7. G. Seitz, T. Kämpchen, Arch. Pharm. 1978, 311, 728.
8. F. A. Khan, B. Prabhudas, J. Dash, J. Prakt. Chem. 2000, 342, 512.
9. H. Isobe, S. Sato, T. Tanaka, H. Tokuyama, E. Nakamura, Org. Lett. 2004, 6, 3569.
10. S. Sato, H. Isobe, T. Tanaka, T. Ushijima, E. Nakamura, Tetrahedron 2005, 61, 11449.
11. CH coupling constants between atoms with underline or by NOE correlations shown in arrows. (Chemical Equation Presented)
12. K. N. Houk, Acc. Chem. Res. 1975, 8, 361;
13. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, Chichester, 1976.
14. HOMO coefficients of A are calculated as shown at HF/6-31G* level, which indicates the preference for the 2:1 adduct 4 over 5. (Chemical Equation Presented)
15. H.-E. Bäckvall, N. K. Plobeck, S. K. Juntunen, Tetrahedron Lett. 1989, 30, 2589.
16. L. Lee, J. K. Snyder, Adv. Cycloaddit. 1999, 6, 119.
17. K. Stott, J. Keeler, Q. N. Van, A. Shaka, J. Magn. Reson. 1997, 125, 302.
18. P. E. Hansen, Prog. Nucl. Magn. Reson. Spectrosc. 1981, 14, 175;
19. N. Matsumori, D. Kaneno, M. Murata, H. Nakamura, K. Tachibana, J. Org. Chem. 1999, 64, 866.
20. A. C. Geoffrey, J. Org. Chem. 1975, 40, 3161.