利用1-(2-炔基苯基)吡咯之環化反應製備吡咯[1,2-a]喹啉

Cyclization of 1-(2-alkynylphenyl)pyrroles to pyrrolo[1,2-a]quinolines

10.6832/KMU.2008.00012

黃民安

吡咯 ； pyrrole

高雄醫學大學醫藥暨應用化學研究所學位論文

2008年

碩士

吳明忠

繁體中文

利用2-炔基溴苯33和吲哚，加入碘化銅當催化劑，製備1-(2-炔基苯基)吲哚35。利用化合物35和催化量的Pd(OAc)2或PdCl2反應，沒有得到任何環化產物。但把化合物35和各種鹵化試劑作用，可得3-鹵吲哚衍生物，產率有15~81%。另一方面，取2-炔基双苯基 42a 和42b 與 碘化芳香烴反應，利用Pd(OAc)2 當催化劑得到環化產物43a 和 45a 產率分別為51% 和 61%。

1-(2-alkynylphenyl)indoles 35 were prepared by the reaction of 2-alkynylbromobenzenes 33 with indole using CuI as a catalyst. Treatment of 35 with catalytic amount of Pd(OAc)2 or PdCl2 did not give any cyclization adduct. However, treatment of 35 with various of halogenating agents gave 3-haloindole derivatives in 15~81% yields. On the other hand, reaction of 2-alkynylbiphenyls 42a and 42b with aryl iodides using Pd(OAc)2 as acatalyst gave the cyclization adducts 43a and 45a in 51% and 61% yields, respectively.