An Isomeric Swapping of a Phenylhydrazone Derivative Discovered by Structural Study Revealing a Branched Pathway of Fischer Indole Synthesis  

作　　者：方昕 于海洋 黄明东 王俊东 

机构地区：[1]College of Chemistry and Chemical Engineering,Fuzhou University [2]Fujian Institute of Research on the Structure of Matter

出　　处：《Chinese Journal of Structural Chemistry》2010年第8期1175-1178,共4页结构化学（英文）

基　　金：Supported by the Natural Science Foundation of Fujian Province (No. 2006 F5058);Fuzhou University (No. XRC-0527)

摘　　要：In an attempt to synthesize an indole derivative,methyl 5-nitro-1H-indole-2-carb-oxylate,an isomeric change of methyl 2-[2-（4-nitrophenyl） hydrazono] propanoate from E to Z geometry was observed.The two isomers were determined by single-crystal X-ray diffraction analysis.The Z isomer is stabilized in a six-membered ring conformation constructed by an intramolecular hydrogen bond.This isomeric change added a branched pathway in the mechanism of Fischer indole synthesis.In an attempt to synthesize an indole derivative,methyl 5-nitro-1H-indole-2-carb-oxylate,an isomeric change of methyl 2-[2-（4-nitrophenyl） hydrazono] propanoate from E to Z geometry was observed.The two isomers were determined by single-crystal X-ray diffraction analysis.The Z isomer is stabilized in a six-membered ring conformation constructed by an intramolecular hydrogen bond.This isomeric change added a branched pathway in the mechanism of Fischer indole synthesis.

关 键 词：Fischer indole synthesis mechanism isomeric change 

分 类 号：O621.3[理学—有机化学]