Abstract
Treatment of 2-[(dimethylamino) methylene]-3-oxobutanoates 9 or 10 with LiN(SiMe 3 ) 2 in the presence of RCOCl results in C-acylation. The resulting intermediate, without isolation, may be converted to 6-R-3-Carbethoxy-4-pyrones (e.g., 12) by H 3 O + or to the corresponding pyridinones (e.g., 13) by NH 4 OAc. Typically, yields are 55-75% for R groups lacking acidic α or γ protons and ca. 30% for R=Me 2 CH or MeCH=CH. Replacing 9 with MeCOC(=CHNMe 2 )SCH 2 Ph (from MeCOCH 2 SCH 2 Ph) and Me 2 NCH(OMe) 2 similarly affords 3-(PhCH 2 S)-substitued products such as 29. Alkylation of the pyridinone anions produces mixtures of N- and O-substituted compounds, with the latter predominating; aminolysis of the isolated pyrones (R'NH 2 -HOAc, where R'-alkyl, Ar, HO, etc.) is the preferred route to the 1-R'-substituted pyridinones
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