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Synthesis 1991; 1991(10): 894-896
DOI: 10.1055/s-1991-26604
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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
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Publication Date:
29 April 2002 (online)

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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)