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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

Abstract

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.

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Copyright information

© Springer-Verlag 1974

Authors and Affiliations

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

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