Keteneおよびその誘導体の研究(第29報) : Quinolizine誘導体の合成

概要

論文の詳細を見る
Ethyl 2-pyridineacetate (IVa) reacts easily with the Vilsmeier reagent to form ethyl α-(dimethylaminomethylene)-2-pyridineacetate (Va) in 50% yield. Similarly, 2-pyridineacetonitrile (IVb), ethyl 2-quinolineacetate (VIa), and 2-quinolineacetonitrile (VIb) undergo the Vilsmeier reaction to form the corresponding enamines, α-(dimethylaminomethylene)-2-pyridineacetonitrile (Vb), ethyl α-(dimethylaminomethylene)-2-quinolineacetate (VIIa), and α-(dimethylaminomethylene)-2-quinolineacetonitrile (VIIb). Va reacts with ketene to form ethyl 4-oxo-4H-quinolizine-1-carboxylate (XII : R=CO_2Et), and with diketene to form ethyl 3-acetyl-4-oxo-4H-quinolizine-1-carboxylate (XVa). Similarly, enamines Vb, VIIa, and VIIb react with diketene to form 3-acetyl-4-oxo-4H-quinolizine-1-carbonitrile (XVb), ethyl 2-acetyl-1-oxo-1H-benzo[c]quinolizine-4-carboxylate (XVIIIa), and its 4-nitrile isomer (XVIIIb). XVa can also be obtained from Va and ethyl acetoacetate, and its reduction with sodium borohydride gives its alcohol derivative (XVII).
公益社団法人日本薬学会の論文
1969-10-25