Journal of Organic Chemistry p. 4963 - 4967 (1991)
Update date:2022-07-29
Topics:
McCombie, Stuart W.
Metz, William A.
Nazareno, Dennis
Shankar, Bandarpalle B.
Tagat, Jayaram
Treatment of 2-<(dimethylamino)methylene>-3-oxobutanoates 9 or 10 with LiN(SiMe3)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 H3O+ or to the corresponding pyridinones (e.g., 13) by NH4OAc.Typically, yields are 55-75percent for R groups lacking acidic α or γ protons and ca. 30percent for R = Me2CH or MeCH=CH.Replacing 9 with MeCOC(=CHNMe2)SCH2Ph (from MeCOCH2SCH2Ph and Me2NCH(OMe)2 similarly affords 3-(PhCH2S)-substituted 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'NH2-HOAc, where R' = alkyl, Ar, HO, etc.) is the preferred route to the 1-R'-substituted pyridinones.
View MoreGoldwills Pharmaceuticals Co., Ltd.
Contact:0916-2237889 13991621155
Address:North Suburb of Hanzhong city, Shaanxi Province
Contact:+86-158-05817090
Address:ROOM 9F, FLAT 2, GUODU DEVELOPING BLDG, No.182, ZHAOHUI ROAD
China Synchem Technology Co.,Ltd
website:http://www.cnsynchem.com
Contact:+86-0552-4929311
Address:No.217 Daqing Road
WuHan rongfashun BioChemical co., LTD
Contact:02788866139
Address:No.95 LuoYu Road,Wuhan
Jintan Jinnuo Chemical Co., Ltd.
Contact:+86-519-80199901
Address:Room 1804, Building 1, Huacheng Business Plaza, Jintan, Jiangsu, China
Doi:10.1016/S0960-894X(98)00697-0
(1999)Doi:10.1021/ja304454r
(2012)Doi:10.1055/s-0040-1706144
(2021)Doi:10.1016/j.tet.2016.05.009
(2016)Doi:10.1021/jo982240r
(1999)Doi:10.1002/(sici)1099-0690(199905)1999:5<1259::aid-ejoc1259>3.0.co;2-n
(1999)