Electronic Effects on the Cyclization of Enediynes

• Main Authors: Yu-Chieh Chen, 陳俞絜
• Other Authors: Ming-Jung Wu
• Format: Others
• Language: zh-TW
• Published: 2018
• Online Access: http://ndltd.ncl.edu.tw/handle/jqgeqr

碩士 === 國立中山大學 === 化學系研究所 === 106 === Recently a series of transition-metal-catalyzed or halomediated cyclizations of enediynes and aryldiynes to give benzofulvenes, dibenzo[b,d]pyran-6-ones, benzo[a]carbazoles, ,benzo[b]naphtho[2,1-d]thiophenes and indeno[1,2-c]chromene have been reported. On the basis of the experimental results, we are able to understand more clearly the electron effect upon the mode of cyclization of these diyne derivatives. In this report, treatment of N-((2-((2-(dimethylamino)phenyl)ethynyl)phenyl) ethynyl)-N-methylmethanesulfonamide (1) with 10 mol% of palladium catalysts and 2 equiv. of copper halide at refluxing acetonitrile gave chloro- and bromosubstituted benzo[a]carbazole derivatives (2a and 2b). Benzo[a]carbazole derivatives (3c) were also generated by treating compound 1 with 10 mol% of Au/Ag catalysts at refluxing benzene.