Cinnoline誘導体に関する研究(第7報)4-CinnolinecarbonitrileとKetone Carbanionとの反応について

概要

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Reaction of 4-cinnolinecarbonitrile (I) with ketones was attempted in benzene, in the presence of sodium amide. In the case of a methyl ketones acetophenone (IIa) and acetone (IIc), the -CN group in 4-position of I was substituted to give 2-(4-cinnolinyl)-acetophenone (IIIa) and 1-(4-cinnolinyl)-2-propanone (IIIc), respectively. In the case of an ethyl ketone, propiophenone (IIb), the reaction product was not isolated, but 4-ethylcinnoline (IV) was obtained when reacted with diethyl ketone (IId). IV was considered to be formed secondarily from 2-(3-cinnolinyl)-3-pentanone (IIId). Reaction of I with methyl ethyl ketone (IIe) afforded two kinds of a product, 1-(4-cinnolinyl)-2-butanone (IIIe) and IV. In this case, also, 3-(4-cinnolinyl)-2-butanone (III'e), thought to be the precursor of IV, was not isolated.
公益社団法人日本薬学会の論文
1974-08-25