An Isomeric Swapping of a Phenylhydrazone Derivative Discovered by Structural Study Revealing a Bran

• 作 者: 方昕 于海洋 黄明东 王俊东
• 机 构: College of Chemistry and Chemical Engineering,Fuzhou University,Fujian Institute of Research on the
• 出 处: 结构化学
• 发表日期: 2010年08期
• 关键词: intramolecular isomers indole conformation derivative membered synthesize Fische

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.