Simultaneous Formation of 8<i>H</i>-Isoquino[2,1-<i>b</i>][2,7]naphthyridin-8-ones and 13<i>H</i>-Pyrido[4′,3′:3,4]pyrrolo[2,1-<i>b</i>][3]benzazepin-13-ones, a Novel Potential Alkaloidal System
作者:Kuppuswamy Nagarajan、Patrick J. Rodrigues、Munirathinam Nethaji、Markus Vöhler、Wolfgang von Philipsborn
DOI:10.1002/hlca.19940770118
日期:1994.2.9
ne (4) with 4-methylnicotinoyl chloride (12) in refluxing pyridine gives 5,6,13,13a-tetrahydro-2,3-dimethoxy-8H-isoquino[2,1-b][2,7] naphthyridin-8-one (11), along with some of its 13,13a-didehydro derivative 7. A similar reaction of 4 with 4-(chloromethyl)nicotinoyl chloride (14) affords, in addition to 7, the isomeric product 10,11-dihydro-7,8-dimethoxy-13H-pyrido[4′,3′:3,4]pyrrolo[2,1- b][3]benzazepin-13-one
3,4-二氢-6,7-二甲氧基异喹啉(4)与4-甲基烟酰氯(12)在回流的吡啶中缩合得到5,6,13,13a-四氢-2,3-二甲氧基-8 H-异喹啉[2] ,1- b ] [2,7]萘啶-8-一(11),以及其13,13a-didehydro衍生物7。4与4-(氯甲基)烟酰氯的类似反应(14)除7外,还提供异构体10,11-dihydro-7,8-dimethoxy-13 H -pyrido [4',3':3 ,4] pyrrolo [2,1- b ] [3] benzazepin-13-one(3)。从3,4-二氢-6,7-(亚甲基二氧基)-和3,4-二氢-6,7,8-三甲氧基-异喹啉(分别为15和18)获得类似的产物对。3的结构通过广泛的NMR数据确定,并通过单晶X射线研究证实。结构7具有像alangimarinc(1)一样的Alangium生物碱的环系统,而根据生物遗传推理,异构环系统3预计会自然存在。