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

• DOI: 10.1021/acs.orglett.8b03090
• Publication Date: 2018-10-18T16:25:35Z
• Authors: Sen Yang; Dengfu Lu; Hengrui Huo; Fan Luo; Yuefa Gong
• Keywords: Enamine; Cyclopropene; Alkyne; Benzoxazole

A one-pot, three-component reaction between alkyl 1-chlorocyclopropanecarboxylate, alkyne diester, and amine is developed. This cascade proceeds smoothly to afford substituted 2-aminophenols in high yields. The process through a formal [3 + 3] cycloaddition an enamine cyclopropene intermediate formed situ. can be transformed into phenoxazines benzoxazole derivatives with the treatment of PIDA.