Revisiting Dimerization of Acetoacetamide Leading to 4,6-Dimethyl-2-pyridone-5-carboxamide

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Dimerization of acetoacetamide leading to 5-carbamoyl-4,6-dimethyl-2-pyridone.

The dimerization of acetoacetamide easily proceeds at room temperature in a dimethyl sulfoxide solution to afford 5-carbamoyl-4,6-dimethyl-2-pyridone.

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5-Methyl-2-pyridone

The crystal structure of the title compound, C(6)H(7)NO, is stabilized by inter-molecular N-H⋯O hydrogen bonds, resulting in inversion dimers. The structure is further consolidated by weak C-H⋯O hydrogen bonds.

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The excretion of N-methyl-2-pyridone-5-carboxamide by man following ingestion of several known or potential precursors.

The development of a rapid method for the determination of N-methyl2-pyridone-5-carboxamide (pyridone) in urine (1) has made it practical to attempt to confirm and extend the studies of Holman and de Lange (2) and others (3-5) concerning the excretion of the pyridone following the administration of various known or possible precursors to man. In the conversion of nicotinic acid to the pyridone ...

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N-Methyl-4-pyridone-5-carboxamide as a metabolite of nicotinic acid in man and monkey.

In previous experiments reported from this laboratory (1) N-methyl-4-pyridone-5-carboxamide was isolated from rat urine and identified as the major urinary metabolite of the pyridine nucleotides. Recently Wieland et al. (2) synthesized this 4-pyridone and have found their synthetic product to be identical with the compound isolated from rat urine. Experiments have now been carried out to determ...

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N-methyl-2-pyridone-5-carboxamide (2PY)—Major Metabolite of Nicotinamide: An Update on an Old Uremic Toxin

N-methyl-2-pyridone-5-carboxamide (2PY, a major metabolite of nicotinamide, NAM) was recently identified as a uremic toxin. Recent interventional trials using NAM to treat high levels of phosphorus in end-stage renal disease have highlighted new potential uremic toxicities of 2PY. In the context of uremia, the accumulation of 2PY could be harmful-perhaps by inhibiting poly (ADP-ribose) polymera...

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ژورنال

عنوان ژورنال: Journal of Oleo Science

سال: 2014

ISSN: 1345-8957,1347-3352

DOI: 10.5650/jos.ess14004