57 エナミドを用いたClavine類の合成研究

概要

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The reaction of cyclohexanone with acrylamide was shown to afford quinolones in one step, which were also prepared from the reaction of cyclohexanoneimine with acryloyl chloride. In order to exploit the route for preparing the clavines (A), which have an indolo[4,3-f,g]quinoline skeleton, some extensions of the above reaction have been studied. As a result, benzo[f]quinolines (8, 10, and 22) were readily prepared either by thermal annelation of 2-tetralone with methacrylamide, or photocyclisation of the methacrylamides (7 and 9) of 2-naphthylamine and the methacrylamide (21) of 2-tetraloneimine. Indolo[4,3-f,g]quinolones (15, 16, 26, and 27) were also prepared either by photocyclisation of the methacrylamide (14) of 4-aminonaphthostyril, annelation of the 4-ketohexahydrobenz[c,d]-indole (23) or its imine (24) with methacrylamide, or more effectively, by acylation of the imine (24) with methacryloyl chloride. The latter reaction yielded a 1: 4 mixture of the uncyclised amide (25) and the cyclised lactam (26), of which (26b) was successfully converted into the 6,8-dimethylergolines (32, 33, and 34), which were identified as costaclavine (32), epicostaclavine (33), and festuclavine (34) respectively. The n.m.r. spectra of four stereoisomers of 6,8-dimethylergoline unambiguously established their stereochemistry.
天然有機化合物討論会の論文
1976-09-20