Structure determination of the products from the acid-catalyzed condensation of indole with acetone

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 451-454

  Noland, Wayland E ^a   Konkel, Michael J ^a   Konkel, Lisa M C ^a   Pearce, Bradley C ^a   Barnes, Charles L ^b   Schlemper, Elmer O ^b  

^a University of Minnesota   (United States)

^b UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAZOLE DERIVATIVE; INDOLE DERIVATIVE;

ARTICLE; DNA SYNTHESIS; DRUG STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030052115     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951596p     Document Type: Article

References (15)

1. Scholtz, M. Ber Dtsch. Chem. Ges. 1913, 46, 1082-1089.
2. Noland, W. E.; Richards, C. G.; Desai, H. S.; Venkiteswaran, M. R. J. Org. Chem. 1961, 26, 4254-4262.
3. Noland, W. E.; Venkiteswaran, M. R.; Lovald, R. A. J. Org. Chem. 1961, 26, 4249-4254.
4. (a) Pearce, Brad C. A Symmetrical Spiro 2:3 Cyclization Product from the Condensation of Indole with Acetone. Paper presented before Session III (Organic) at the 21st Annual Undergraduate Symposium in Chemistry (sponsored by the Minnesota Section of the American Chemical Society), University of Wisconsin at River Falls, April 28, 1979.
5. 5 while acknowledging our contribution. Our new data for compound 2a are provided in the Experimental Section.
6. Bergman, J.; Norrby, P.-O.; Tilstam, U.; Venemalm, L. Tetrahedron 1989, 45, 5549-5564.
7. Banerji, J.; Chatterjee, A.; Manna, S.; Pascard, C.; Prangé, T.; Shoolery, J. N. Heterocycles 1981, 15, 325-336.
8. Chatterjee, A.; Manna, S.; Banerji, J.; Pascard, C.; Prangé, T.; Shoolery, J. N. J. Chem. Soc., Perkins Trans, 1 1980, 553-555.
9. Johnson, C. K. ORTEP II. Report ORNL-5138; Oak Ridge National Laboratory, TN, 1976.
10. Electrophilic substitution at the 2-position of 3-alkylindoles has been previously observed. A few examples include: (a) Noland, W. E.; Robinson, D. N. Tetrahedron 1958, 3, 68-72 (b) St. C. Black, D.; Craig, D. C.; Kumar, N. J Chem. Soc., Chem. Commun. 1989, 425-426 (c) St. C. Black, D.; Craig, D. C.; Kumar, N. Tetrahedron Lett. 1991, 32, 1587-1590.
11. Electrophilic substitution at the 2-position of 3-alkylindoles has been previously observed. A few examples include: (a) Noland, W. E.; Robinson, D. N. Tetrahedron 1958, 3, 68-72 (b) St. C. Black, D.; Craig, D. C.; Kumar, N. J Chem. Soc., Chem. Commun. 1989, 425-426 (c) St. C. Black, D.; Craig, D. C.; Kumar, N. Tetrahedron Lett. 1991, 32, 1587-1590.
12. Electrophilic substitution at the 2-position of 3-alkylindoles has been previously observed. A few examples include: (a) Noland, W. E.; Robinson, D. N. Tetrahedron 1958, 3, 68-72 (b) St. C. Black, D.; Craig, D. C.; Kumar, N. J Chem. Soc., Chem. Commun. 1989, 425-426 (c) St. C. Black, D.; Craig, D. C.; Kumar, N. Tetrahedron Lett. 1991, 32, 1587-1590.
13. International Tables for X-ray Crystallography; Kynoch Press: Birmingham U.K. (present distributor D. Reidel: Dordrecht, Neth.), 1974; Vol. IV.
14. Gabe, E. J.; Le Page, Y.; Charland, J.-P.; White, P. S. J. Appl. Crystallogr. 1989, 22, 384-387.
15. The authors have deposited the atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, upon request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.