The crystal structure of a novel product from the acid-catalyzed condensation of 1-benzylindole with acetone

Journal of Chemical Crystallography

Volumn 29, Issue 1, 1999, Pages 9-14

  Noland, Wayland E ^a   Konkel, Michael J ^a   Fanburg, Susan J ^a   Venkatraman, Shankar ^a   Britton, Doyle ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

1 benzylindole; Acetone; Spiro cyclopent b indole

Indexed keywords

EID: 0033244862     PISSN: 10741542     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1009506927964     Document Type: Article

References (21)

1. Scholtz, M. Ber. Dtsch. Chem. Ges. 1913, 46, 1082.
2. Noland, W.E.; Richards, C.G.; Desai, H.S.; Venkiteswaran, M.R. J. Org. Chem. 1961, 26, 4254.
3. Noland, W.E.; Konkel, M.J.; Konkel, L.M.C.; Pearce, B.C.; Barnes, C.L.; Schlemper, E.O. J. Org. Chem. 1996, 61, 451.
4. Noland, W.E.; Venkiteswaran, M.R.; Richards, C.G. J. Org. Chem. 1961, 26, 4241.
5. Noland, W.E.; Venkiteswaran, M.R.; J. Org. Chem. 1961, 26, 4263.
6. Chatterjee, A.; Manna, S.; Banerji, J.; Pascard, C.; Prange, T.; Shoolery, J.N. J. Chem. Soc. Perkin Trans. I 1980, 553.
7. Banerji, J.; Chatterjee, A.; Manna, S.; Pascard, C.; Prange, T.; Shoolery, J.N. Heterocycles 1981, 15, 325.
8. Bergman, J.; Norrby, P.-O.; Tilstam, U.; Venemalm, L. Tetrahedron 1989, 45, 5549.
9. Noland, W.E.; Wann, S.R. J. Org. Chem. 1979, 44, 4402.
10. Noland, W.E.; Condoluci, M.J.: Konkel, M.J.; Brigham, M.E.: Trowbridge, A.G.; Konkel, L.M.C.; Gourneau, R.P.; Scholten, C.A.; Lee, N.H.; Condoluci, J.J.; Gac, T.S.; Mostafaei Pour, M.: Radford, P.M. J. Heterocycl. Chem. 1993, 30, 81.
11. Heaney, H.; Ley, S.V. In Organic Syntheses; Coll. Vol. VI, Noland, W. E., Ed.: Wiley: New York, 1988; pp 104-105.
12. For other examples of bisindole formation from acid-catalyzed condensations of indoles with carbonyls, see refs. 4, 5, 8 and the following: (a) Noland, W.E.; Robinson, D.N. J. Org. Chem. 1957, 22, 1134.
13. (b) Noland, W.E.; Robinson, D.N. Tetrahedron 1958, 3, 68.
14. Noland, W.E.; Venkiteswaran, M.R.; Lovald, R.A. J. Org. Chem. 1961, 26, 4249.
15. Noland, W.E.; Richards, C.G.; Dessai, H.S.; Venkiteswaran, M.R. J. Org. Chem. 1961, 26, 4254.
16. The reversibility of formation of a different bisindole in warm acetic anhydride has been observed (ref. 4).
17. TEXSAN. TEXRAY Structure Analysis Package.; MSC. The Woodlands: Texas, 1985.
18. Gilmore, C.J. J. Appl. Cryst. 1984, 17, 42-46.
19. Beurskens, P.T. DIRDIF: Direct Methods for Difference Structures; Technical Report 1984/1, Crystallography Laboratory, Toernooiveld, 6525 Ed Nijmegen, Netherlands, 1984.
20. Abrahams, S.C.; Keve, E.T. Acta Crystallogr. 1971 A27, 157.
21. DeCamp, W.H. Acta Crystallogr. 1973, A29, 148.