Abstract
The Vilsmeier reaction of phenylacetonitriles to obtain intermediates of isoquinoline cyclization was described (refer to Chart 1). Phenylacetonitrile (I) gave β-dimethylamino-α-phenylacrylonitrile (II), α-formyl-(III) and α, N-diformyl- (IV) α-phenylacetamide, and 5, 7-dioxo-2, 6-diphenyl-4-aza-2-heptenamide (VI). m-Methoxyphenylacetonitrile (VII) gave α-(m-methoxyphenyl)-β-dimethylaminoacrylonitrile (VIII) and 3, 5-bis (m-methoxyphenyl)-6-(N, N-dimethylaminomethyleneamino)-2(1H)-pyridone (IX). p-Methoxyphenylacetonitrile (XI) gave 2-[α-(β-carbamoyl)-p-methoxystyryl) amino]-6-chloro-3, 5-bis(p-methoxyphenyl) pyridine (XII). 3, 5-Dimethoxyphenylacetonitrile (XIV) gave 3-chloro-6, 8-dimethoxyisoquinoline (XV) and 3-chloro-5-hydroxymethyl-6, 8-dimethoxyisoquinoline (XVI). Phenylacetamides (V, X, XIII, XVII) were also obtained from respective nitriles (I, VII, XI, XIV).
