Process for preparing 5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-p

Details Process for preparing 5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-p Process for preparing 5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-p

1982-03-15

1983-10-25

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546288, 568307, C07D21350

Patent

active

044120770

ABSTRACT:
4-R.sub.2 -5-(Lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones (I), useful as cardiotonics, where R.sub.2 is hydrogen or methyl, are prepared by reacting 2-(lower-alkanoyl)-1-(lower-alkyl)ethenamine (II) with lower-alkyl 2-propynoate or 2-butynoate respectively or by hydrolyzing 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinonitrile (III, Q is CN) or corresponding 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinamide to produce the corresponding 5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinic acid and decarboxylating said substituted nictotinic acid to produce I. Also disclosed and claimed are cardiotonic uses of 3-Q-4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones where Q is hydrogen or cyano and R.sub.2 is hydrogen or methyl (III). Also shown and claimed is methyl 4-acetyl-5-amino-2,4-hexadienoate or acid-addition salt thereof, useful as intermediate or cardiotonic.

REFERENCES:
patent: 3654291 (1972-04-01), Witzel et al.
Sunthankar et al. [Indian J. of Chem. 11, 1315-1316 (1973)].
Kato et al. [J. Heterocyclic Chem. 18, 603-606 (1981)].
Kato et al. [Chem. Pharm. Bull. 17, 2411-2416 (1969)].
Fujita [Chem. Pharm. Bull. 23, 501-506 (1975)].
Krasnaya et al [C.A. 87, 68099r (1977)].

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