Generation and in situ acylation of enaminone anions: a convenient synthesis of 3-carbethoxy-4 (1H)-pyridinones and-4-pyrones and related compounds

SW McCombie, WA Metz, D Nazareno…

文献索引：McCombie, Stuart W.; Metz, William A.; Nazareno, Dennis; Shankar, Bandarpalle B.; Tagat, Jayaram Journal of Organic Chemistry, 1991 , vol. 56, # 16 p. 4963 - 4967

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被引用次数: 30

摘要

Treatment of 2-[(dimethylamino) methylene]-3-oxobutanoates 9 or 10 with LiN (SiMe& in the presence of RCOCl results in C-acylation. The resulting intermediate, without isolation, may be converted to 6-R 3-Carbethoxy-4-pyrones (eg, 12) by HSO+ or to the corresponding pyridinones (eg, 13) by NHIOAc. Typically, yields are 55-75% for R groups lacking acidic a or y protons and ca. 30% for R= Me2CH or MeCH= CH. Replacing 9 with MeCOC (= ...