Chinese Journal of Organic Chemistry >
Metal-Free Formation of 2-Substitued Benzoxazoles with Amides and Esters
Received date: 2021-11-22
Revised date: 2022-02-08
Online published: 2022-02-25
Supported by
National Natural Science Foundation of China(21703061); Science and Technology Innovation Program of Hunan Province(2021RC5028)
2-Substituted benzoxazoles are important heterocyclic motifs due to their wide application in pharmacology. A PCl3-mediated C(2)-functionalization of benzoxazole derivatives with inert amides and esters under metal-free conditions was reported. By using PCl3/I2 combination, various 2-substituted benzoxazoles could be synthesized via the arylation or alkylation of benzoxazoles with amides and esters in the presence of water. What’s more, the reactivity between amides and esters was also investigated. The primary results indicated that amides have higher reactivity than esters under this system. This method features a broad substrate scope, simple condition and low-cost. A plausible mechanism was also proposed.
Key words： 2-substituted benzoxazoles; amide; ester; metal-free; phosphorus trichloride
Fangshao Li , Jing Xiao , Xiaofang Wu , Xiaoyi Wang , Jinfeng Deng , Zilong Tang . Metal-Free Formation of 2-Substitued Benzoxazoles with Amides and Esters[J]. Chinese Journal of Organic Chemistry, 2022 , 42(6) : 1778 -1785 . DOI: 10.6023/cjoc202111031
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