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  • Title: Copper(II)-catalyzed Synthesis of Benzoxazoles from Inactive 2-chloroanilides.
    Author: Jiang Y, Tang Y, Gao H, Rao G, Mao Z.
    Journal: Curr Org Synth; 2022; 19(7):819-823. PubMed ID: 35232362.
    Abstract:
    AIM AND OBJECTIVE: Benzoxazoles are of great importance in natural products, pharmaceutical agents as well as synthetic intermediates. Although many works on the construction of benzoxazoles by Cu-catalyzed intramolecular O-arylation of ortho-haloanilides have been reported, only a few reports about transition metal-catalyzed synthesis of benzoxazoles from inactive 2-chloroanilides so far. This work aimed to explore a green and cheap protocol for intramolecular O-arylation of inactive 2-chloroanilides to prepare 2-arylbenzoxazoles. MATERIALS AND METHODS: We found that Cu(acac)2/1,10-Phen complex was beneficial to intramolecular O-arylation of 2-chloroanilides using K2CO3 as a base in EtOH at 90 °C to prepare benzoxazoles. RESULTS: An efficient and green method was developed for Cu(II)-catalyzed intramolecular Oarylation of inactive 2-chloroanilides. CONCLUSION: In this way, many 2-arylbenzoxazoles were prepared in good yields.
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