- N-3-oxoalkylamides and -thioamides in the synthesis of heterocyclic compounds. 7*. Study of the cyclization of N-(3-oxoalkyl)amides of tosylacetic acid
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Alkyl-substituted N-(3-oxoalkyl)amides of tosylacetic acid are cyclized under the action of bases with the formation of 3-tosyl-3,6-dihydropyridin-2(1H) -ones. In the presence of a phenyl substituent at position C(1) of the 3-oxoalkyl chain the
- Fisyuk,Poendaev
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p. 895 - 900
(2007/10/03)
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- Process for the production of 6-substituted 4-methyl-2-pyridones
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Process for the production of 6-substituted-4-methyl-2-pyridones having the formula: STR1 wherein R is a branched or unbranched alkyl group, a halogenated branched or unbranched alkyl group or a substituted or unsubstituted aryl group. Senecioic acid amide having the formula: STR2 is reacted in a solvent at an elevated temperature in the presence of a Lewis acid (as a catalyst) with an acyl chloride having the formula: STR3 wherein R has the same meaning as above. The reaction mixture is subsequently placed in an aqueous phase for hydrolysis. The 6-substituted-4-methyl-2-pyridone is separated by extraction through the buffering of the reaction mixture at a pH of 4 to 5.
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- Synthesis of Methylpyridine Derivatives. XXXIV. Condensation of Acetoacetamide with Ketones to form Pyridone Derivatives
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Condensation of acetoacetamide (1) with acetone in polyphosphoric acid (PPA) gave 4,6-dimethyl-2(1H)-pyridone (2a) in 32percent yield.Similarly, the amide 1 was condensed with 2-butanone, 2-pentanone, 3-pentanone, cyclopentanone, cyclohexanone, cycloheptanone, acetophenone, and propiophenone to give the corresponding pyridone derivatives (2b-i) in 13-76percent yields.Condensation of the amide 1 with acetylacetone and ethyl acetoacetate gave 3-acetyl-4,6-dimethyl-2(1H)-pyridone (5) and ethyl 4,6-dimethyl-2(1H)-pyridone-5-carboxylate (6), respectively.Self-condensation of the amide 1 in PPA gave 3-acetyl-4-hydroxy-6-methyl-2(1H)-pyridone (7).
- Kato, Tetsuzo,Sato, Masayuki,Noda, Masaki,Itoh, Tetsuo
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p. 2244 - 2247
(2007/10/02)
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