Reactivity of 5-(3-azidophenyl)-1-(1 H -pyrrol-3-yl)pyrroles in TFMSA. A route for new ring systems as DNA-interactive agents
作者:Francesco Mingoia
DOI:10.1016/s0040-4020(01)01033-x
日期:2001.12
Acid catalyzed decomposition of 5-(3-azidophenyl)-1-(1H-pyrrol-3-yl)pyrroles did not afford the expected dipyrrolo[2,1-a:3,4-c]isoquinoline derivatives, but the planar dipyrrolo[2,1-a:3,2-c]isoquinoline derivatives and related non planar derivatives 11bH-dipyrrolo[2,1-a:3,2-c]isoquinoline derivatives. In strong acid media (trifluoromethanesulfonic acid) the α-(1-pyrrol-3yl) position even if blocked
5-(3-叠氮基苯基)-1-(1 H-吡咯-3-基)吡咯的酸催化分解未得到预期的二吡咯并[2,1- a:3,4- c ]异喹啉衍生物,但呈平面状双吡咯并[2,1- a:3,2- c ]异喹啉衍生物和相关的非平面衍生物11b H-双吡咯并[2,1- a:3,2- c ]异喹啉衍生物。在强酸介质(三氟甲磺酸)中,α-(1-吡咯-3基)位置即使被封闭,相对于游离β1而言也更容易发生环化。尽管存在位阻,但根据1-(1)上取代基的性质和位置,可以以中等到良好的总收率获得这些化合物H-吡咯基)部分。