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Molecular and crystal structures of a tricyclic γ-lactam ketone and its Mannich base

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Abstract

A tricyclic γ-lactam ketone, 1,10a-Dihydropyrrolo[1,2]isoquinoline-3,10(2H,5H)-dione, and its corresponding Mannich base, 10a-(Dimethylaminomethyl)-1,10a-dihydropyrrolo[1,2b]isoquinoline-3,10(2H,5H)-dione hydrochloride, have been synthesized. The molecular and crystal structures of both compounds were studied by NMR-spectroscopy and X-ray crystallography. Unit cell parameters are:a=8.799(7),b=7.137(6),c=16.156(8)Å,β=76.28(5)°, space groupP21/c forthe first compound, anda=15.343(9),b=7.490(6),c=13.465(8) Å,β=110.98(3)°, space groupP21/c for the second. The structures were refined to discrepancy factorsR=0.068 for 1261 andR=0.047 for 2138 observed CuK α data, respectively. The conversion of the tricyclic γ-lactam ketone to its corresponding Mannich base does not affect thecis configuration between the fused tetrahydropyridine and γ-lactam rings, but does result in conformational changes in both rings.

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References

  • Birnbaum, K. B. (1970)Acta Cryst. B 26, 722–734.

    Google Scholar 

  • Emge, T. J., Strickland, L. C., and Perkins, C. M. (1990)Acta Cryst. C 46, 286–290.

    Google Scholar 

  • Hamilton, W. C. (1959)Acta Cryst. 12, 609–610.

    Google Scholar 

  • Miquel, C., Pigache, P., Rigo, B., and Kolocouris, N. (1980)J. Heterocyclic Chem. 17, 1447–1453.

    Google Scholar 

  • Rigo, B., and Kolocouris, N. (1983)J. Heterocydic Chem. 20, 893–898.

    Google Scholar 

  • Rigo, B., deQuillacq, J., Fossaert, E., and Kolocouris, N. (1984)J. Heterocydic Chem. 21, 1393–1396.

    Google Scholar 

  • Sheldrick, G. M. (1976)Shelx76. Program for crystal structure determination, University of Cambridge, England.

    Google Scholar 

  • Sheldrick, G. M. (1985) In “Crystallographic Computing 3” (G. M. Sheldrick, C. Kruger, and R. Goddard (eds.), Oxford University Press, pp. 175–189.

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Authors and Affiliations

  1. Department of Pharmacy, Division of Pharmaceutical Chemistry, University of Athens, Panepistimiopolis, 157.51, Athens, Greece

    A. Kolocouris, N. Kolocouris, G. B. Foscolos & G. Fytas

  2. Department of Biochemistry, University of Toronto, Faculty of Medicine, M5S 1A8, Toronto, Canada

    A. Hempel & N. Camerman

  3. Departments of Medicine (Neurology) and Pharmacology, University of Washington, 98195, Seattle, Washington

    A. Camerman

  4. Department of Biochemistry, Cell and Molecular Biology and Genetics, University of Athens, Panepistimiopolis, 157 01, Athens, Greece

    S. J. Hamodrakas

Authors
  1. A. Kolocouris
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  2. N. Kolocouris
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  3. G. B. Foscolos
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  4. G. Fytas
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  5. A. Hempel
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  6. N. Camerman
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  7. A. Camerman
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  8. S. J. Hamodrakas
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Kolocouris, A., Kolocouris, N., Foscolos, G.B. et al. Molecular and crystal structures of a tricyclic γ-lactam ketone and its Mannich base. Journal of Crystallographic and Spectroscopic Research 23, 663–667 (1993). https://doi.org/10.1007/BF01325191

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  • DOI: https://doi.org/10.1007/BF01325191

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