- 作者: 林志達 ; 方俊民
- 作者服務機構: 台灣大學化學系
- 中文摘要: 2-Cyano-1-phenylsulfonylindole (1a) and 2-cyano-1- methylindole (1b) were prepared by chemical and electrolytic methods in modest yields. Nucleophiles such as sodium benzenethiolate, butyllithium and lithium dimethylcuprate attacked the sulfonyl group of (1a), whereas they attacked the cyano group of (1b). 1,3-Dipolar cycloadditions of (1a) and (1b) with 2,4,6- trimethylbenzonitrile oxide occurred at the cyano groups. Electrophilic reactions of (1b) with N-bromosuccinimide, Vilsmeir reagent and acetyl chloride afforded the corresponding 3-bromo-, 3-formyl- and 3-acetylindole derivatives in modest or high yields, albeit less rapidly than the reactions of 1-methylindole. Photochemical addition of dimethyl acetylenedicarboxylate to (1b) was followed by cleavage of the cyclobutene intermediate to give dimethyl(2-cyano-1-methylbenzazepine)-3,4-dicarboxylate.
- 英文摘要: --
- 中文關鍵字: Cyanoindole; Electrophilic Reaction; Nucleophilic Reaction; Diels-Alder Reaction; Dipolar Cycloaddition; Photochemistry
- 英文關鍵字: 氰基;親電子反應;親核反應;Diels-Alder反應;雙極化環加成反應;光化學