Monatshefte für Chemie / Chemical Monthly

, Volume 105, Issue 1, pp 196–202 | Cite as

Pyrindinchemie, 2. Mitt.: Über die Synthese des 5,6-Dihydro-2-pyrindin-7-ons

  • D. Binder
Organische Chemie und Biochemie

The synthesis of 5.6-dihydro-2-pyrindin-7-one


The reaction of cinchomeronic anhydride with diethyl malonate in acetic anhydride in the presence of triethylamine yields1, which is hydrogenated over Pd/C (10%) in dry benzene to2. The structures of1 and2 are confirmed by IR-and1H-NMR-spectra.1 can be reduced to3 with Zn in acetic acid. Hydrolysis of3 yields4, which is easily decarboxylated to5. Methylation of5 with CH2N2 gives6. The1H-NMR-spectrum of6 makes a definite structural assignment possible.6 undergoes a Dieckmann cyclisation to7, which forms8 on heating in water, and the title compound9 on heating in 4n-HCl.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Ch. Ruangsiyanand, H. J. Rimek undF. Zymalkowski, Chem. Ber.103, 2403 (1970).Google Scholar
  2. 2.
    D. Binder, Mh. Chem.105, 179 (1974).Google Scholar
  3. 3.
    V. Oskaja undG. Vanags, Latvyas PSR Zinatnu, Akad. Vestis Kim. Ser.1964, 271.Google Scholar
  4. 4.
    J. Wislicenus, Ann. Chem.242, 32 (1887).Google Scholar
  5. 5.
    J. Scheiber, Ann. Chem.389, 125 (1912);K. Auwers undE. Auffenberg, Ber. dtsch. chem. Ges.51, 1106 (1918);J. Scheiber undG. Hopfer, Ber. dtsch. chem. Ges.53, 898 (1920).Google Scholar
  6. 6.
    J. Suszko undS. Kinastowski, Bull. Acad. Polon. Sci., Ser. Sci. Chim.14, 157 (1966), Roczn. Chem.41, 111 (1967).Google Scholar
  7. 7.
    K. Schofield, Hetero-aromatic nitrogen compounds: Pyrroles and Pyridines, S. 323: Butterworth. 1967.Google Scholar
  8. 8.
    J. H. Bobbitt undD. A. Scola, J. Org. Chem.25, 560 (1960).Google Scholar

Copyright information

© Springer-Verlag 1974

Authors and Affiliations

  • D. Binder
    • 1
  1. 1.Institut für Organische Chemie der Technischen Hochschule WienWienÖsterreich

Personalised recommendations