1-Acetylirrüno-3-methyl-1H-isochromene-4-carbonitrile, 1, reacts with glycine ethyl ester under basic conditions to give an imidazo[2,1-a]isoquinoline derivative, while reaction with hydrazine hydrate in 1,4-dioxane, with further chemistry, provides access to [1,2,4]triazolo[5,1-a]isoquinoline, [1,2,4]triazolo[3,4-a]isoquinoline and tetrazolo[5,1-a]isoquinoline analogs. Benzene ring nitration and radical bromination of substituent methyl groups were investigated in the four tricycles, with some different positional reactivities being found. Two bromomethyl derivatives so produced were oxidised; ethyl 2-bromomethyl-6-cyano-5-methylimidazo[2,1-a]isoquinoline-3-carboxylate gave the anticipated ethyl 6-cyano-2-formyl-5-methylimidazo[2,1-a]isoquinoline-3-carboxylate (which reacted further with hydrazine to form a new system, 8,9-dihydro-6-methyl-8-oxopyridazino[4′,5′:4,5]imidazo[2,1-a]isoquinoline-5-carbonitrile), while 5-bromomethyl-2-methyl[1,2,4]triazolo[5,1-a]isoquinoline-6-carbonitrile unexpectedly gave directly another new system, 5,6-dihydro-5-hydroxy-2-methyl-7H-pyrrolo[3,4-c][1,2,4]triazolo[5,1-a]isoquinolin-7-one.

中文翻译：

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咪唑，三唑和四唑异喹啉衍生物的合成和反应性

1-Acetylirrüno-3-甲基-1 H-异亚甲基-4-甲腈1在碱性条件下与甘氨酸乙酯反应生成咪唑并[2,1- a ]异喹啉衍生物，而与水合肼在1,4中反应-二恶烷，具有进一步的化学性质，提供了与[1,2,4]三唑并[5,1- a ]异喹啉，[1,2,4]三唑并[3,4- a ]异喹啉和四唑[5,1- a ]异喹啉类似物。在四个三环中研究了取代基甲基的苯环硝化和自由基溴化，发现了一些不同的位置反应性。如此生成的两种溴甲基衍生物被氧化。乙基2-溴甲基-6-氰基-5-甲基咪唑[2,1- a]异喹啉-3-羧酸酯得到预期的6-氰基-2-甲酰基-5-甲基咪唑并[2,1- a ]异喹啉-3-羧酸乙酯（它与肼进一步反应形成新体系8,9-二氢-6-甲基-8-氧代吡啶并[4'，5'：4,5]咪唑并[2,1- a ]异喹啉-5-甲腈），而5-溴甲基-2-甲基[1,2,4]三唑并[5,1- a ]异喹啉-6-腈出乎意料地直接提供了另一个新系统，5,6-二氢-5-羟基-2-甲基-7 H-吡咯并[3,4- c ] [1,2,4 ] triazolo [5,1- a ]异喹啉-7-一。