Download PDF
Synthesis 1991; 1991(10): 894-896
DOI: 10.1055/s-1991-26604
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of 3-Methyl and 7-Methyl Regio Isomers of Medorinone

Baldev Singh* , George Y. Lesher, Ruth P. Brundage
  • *Department of Medicinal Chemistry, Sterling Research Group, Rensselaer, N.Y. 12144, USA
Further Information

Publication History

Publication Date:
29 April 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Reaction of 3-aminocrotononitrile (2) with methyl methacrylate (3) and methyl 2-propynolate (9) led to the formation of 1,4,5, 6-tetrahydro-2,5-dimethyl-6-oxo-3-pyridinecarbonitrile (4) and 1, 6-dihydro-2-methyl-6-oxo-3-pyridinecarbonitrile (10), respectively. Condensation of 4 with Bredereck's reagent [bis(dimethylamino)-tert-butoxymethane], and that of 6-methoxy-2-methyl-3-pyridinecarbonitrile (12) with N,N-dimethylacetamide dimethyl acetal gave the corresponding enamines 5 and 13 which in turn were cyclized with hydrogen bromide to bromonaphthyridinones 6 and 14, respectively. Debromination of 6 followed by dehydrogenation gave 3-methyl-1,6-naphthyridin-2(1H)-one (8). Debromination of 14 with catalytic reduction gave 7-methyl-1, 6-naphthyridin-2(1H)-one (15)

      >