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

【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.更多还原

【Abstract】 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.更多还原