- Synthesis of 3-methyl and 7-methyl regio isomers of medorinone
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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).
- Singh,Lesher,Brundage
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- 2-[2-(di-lower-alkylamino)-1-propenyl]-6-methoxy-3-pyridinecarbonitriles, intermediates for cardiotonic agents
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2-[2-(di-lower-alkylamino-1-propenyl]-6-methoxy-3-pyridinecarbonitriles, useful as intermediates for cardiotonic agents.
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- 1,6-naphthyridine-2(1H)-ones and their use as cardiotonic agents
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5-X-7-R'-1,6-Naphthyridine-2(1H)-ones (formula II) or salts thereof, where X is bromo, chloro or hydrazino and R' is hydrogen or methyl, which are useful as cardiotonic agents.
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