安定イオウイリドの研究(第9報)Dimethylsulfonium AcetylcarbamoylmethylideとIsoquinoline 2-Oxideとの反応

抄録

The reaction of dimethylsulfonium acetylcarbamoylmethylide (1) with isoquinoline 2-oxide (2) in the presence of acetyl chloride gave 2-[1(2H)-isoquinolylidenemethyl]-6-methyl-5-methylthio-1, 3-oxazin-4-one (3). When 3 was treated with mineral acid, 3-hydroxy-2-(1-isoquinolyl)-3-methyl-4-methylthioglutarimide (10) was obtained as a ring transformation product. 10 was dehydrolized with acid catalyst to 6-hydroxy-3-[1(2H)-isoquinolylidene]-4-methyl-5-methylthiopyridin-2(3H)-one (11). The treatment of 3 with diethylamine (or ethanolic potassium hydroxide) gave 2-diethylamino (or hydroxy)-4-oxopyrimido[4, 3-a]isoquinoline (17 or 18). On the reaction of 3 with acetic anhydride, 2-[1 (2H)-isoquinolylidene]-3-oxobutanenitrile (16) was obtained as a ring opening product.