1,6-π-Electrocyclization of 3-Vinyl-Functionalized N,N′-Dimethyl-2,2′-Bisindolyl: Some Analysis of the Educt Transformation Process

Journal of Heterocyclic Chemistry

Volumn 35, Issue 1, 1998, Pages 97-101

  Pindur, U ^a   Kim, Y S ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLEACETIC ACID; REBECCAMYCIN; STAUROSPORINE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; DRUG TRANSFORMATION; NONHUMAN; PHOTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0031942735     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570350118     Document Type: Article

References (13)

1. G.W. Gribble and S. J. Berthel, A Survey of Indolo[2,3-a]carbazole Alkaloids Related to Natural Products in Studies in Natural Products Chemistry 12, Atta-ur Rahman, ed, Elsevier, Science Publishers, Amsterdam, 1993 pp 365-409.
2. G. W. Gribble, Synthesis and Antitumor Activity of Ellipticine Alkaloids and Related Compounds in The Alkaloids, Vol 30, A. Brossi, ed, Academic Press, New York, 1990 pp 293-352.
3. G. Desimoni, G. Tacconi, A. Barco and G. P. Pollini, Natural Product Synthesis Through Pericyclic Reactions, American Chemical Society Monographs 180, American Chemical Society, Washington DC, 1983.
4. U. Pindur, Cycloaddition with Indole Derivatives in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, Greenwich, CT, 1995 pp 122-170.
5. E. Gonzalez, U. Pindur and D. Schollmeyer, J. Chem. Soc., Perkin Trans 1, 1767 (1996).
6. U. Pindur, Y.-S. Kim and D. Schollmeyer, J. Heterocyclic Chem., 31, 377 (1994)
7. U. Pindur, Y.-S. Kim and D. Schollmeyer, J. Heterocyclic Chem., 32, 1335 (1995).
8. U. Pindur, Y.-S. Kim and D. Schollmeyer, Heterocycles, 38, 2267 (1994).
9. U. Pindur and Y-S. Kim, J. Heterocylic Chem., 33, 623 (1996).
10. For an excellent review on electrocyclization reactions for synthesis of carbazoles see: T. Kawasaki and M. Sakamoto, J. Indian J. Chem. Soc., 71, 443 (1994).
11. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley & Sons, Limited, Chichester, 1976; MOPAC 6.0 (QCPE 504) was used for calculating the frontier orbitals; for details see J. J. P. Stewart, J. Computer-Aided Molecular Design, 4, 1 (1990). The calculations predict that the thermally induced cyclisation is a HOMO controlled disrotatory process and the photochemically induced cyclisation is a LUMO controlled conrotatory process [7].
12. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley & Sons, Limited, Chichester, 1976; MOPAC 6.0 (QCPE 504) was used for calculating the frontier orbitals; for details see J. J. P. Stewart, J. Computer-Aided Molecular Design, 4, 1 (1990). The calculations predict that the thermally induced cyclisation is a HOMO controlled disrotatory process and the photochemically induced cyclisation is a LUMO controlled conrotatory process [7].
13. H. G. Becker, Einfuhrung in die Photochemie, Deutscher Verlag der Wissenschaften, 1991.