Construction of Substituted 2‑Aminophenols via Formal [3 + 3] Cycloaddition of Alkyl 2‑Aroyl-1-chlorocyclopropanecarboxylate with in Situ Generated Enamines

A one-pot, three-component reaction between alkyl 1-chlorocyclopropanecarboxylate, alkyne diester, and amine is developed. This cascade reaction proceeds smoothly to afford substituted 2-aminophenols in high yields. The process proceeds through a formal [3 + 3] cycloaddition between an enamine and a...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2018-11, Vol.20 (21), p.6943-6947
Main Authors: Yang, Sen, Lu, Dengfu, Huo, Hengrui, Luo, Fan, Gong, Yuefa
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A one-pot, three-component reaction between alkyl 1-chlorocyclopropanecarboxylate, alkyne diester, and amine is developed. This cascade reaction proceeds smoothly to afford substituted 2-aminophenols in high yields. The process proceeds through a formal [3 + 3] cycloaddition between an enamine and a cyclopropene intermediate formed in situ. The substituted 2-aminophenols can be transformed into phenoxazines and benzoxazole derivatives with the treatment of PIDA.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03090