Abstract
In order to clarify the mechanism of Fischer indolization of 2-methoxyphenylhydrazones, Fischer indolization of ethyl pyruvate 2-(2-methoxyphenyl)phenylhydrazone (2) was carried out with hydrochloric acid in ethanol and zinc chloride in acetic acid. The reactions proceeded smoothly to give N-arylindoles (11-14) and some chlorinated diphenylamine derivatives (8-10) as by-products. Consideration of the indole products revealed that the Fischer indolization proceeded mainly at the unsubstitued phenyl nucleus rather than at the 2-methoxyphenyl nucleus. This result is inconsistent with the previous result that Fischer indolization of diarylhydrazones proceeded at the electron-richer nucleus. The structures of the diphenylamines were determined by chemical means and the mechanism of their formation is discussed.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
