Construction of N-Ferrocene Substituted Benzodihydrooxazoles via a Catalyst-Free Aza-Michael Addition/C(sp3)-O Bond Formation Tandem Reaction

Mingliang Zhang; Pin Zhao; Qilv Liu; Xinlei Liu; Jingya Hu; Dongqing Wu; Lantao Liu

doi:10.3390/molecules28145615

Construction of N-Ferrocene Substituted Benzodihydrooxazoles via a Catalyst-Free Aza-Michael Addition/C(sp³)-O Bond Formation Tandem Reaction

Molecules. 2023 Jul 24;28(14):5615. doi: 10.3390/molecules28145615.

Authors

Mingliang Zhang¹, Pin Zhao², Qilv Liu¹, Xinlei Liu¹, Jingya Hu¹, Dongqing Wu¹, Lantao Liu^{1

2}

Affiliations

¹ Henan Engineering Research Center of Green Synthesis for Pharmaceuticals, School of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000, China.
² College of Chemistry, Zhengzhou University, Zhengzhou 450052, China.

Abstract

A catalyst-free aza-Michael addition/C(sp³)-O bond formation tandem reaction of substituted amino ferrocenes with quinone esters was developed, which provided a green and efficient strategy for the construction of a C(sp³)-O bond from C(sp³)-H, and a series of N-ferrocene-substituted benzodihydrooxazoles were smoothly produced in moderate to excellent yields (up to >99% yield). The mechanism experiments showed that quinone esters performed as both substrate and oxidant. The salient features of this transformation include good functional group tolerance, broad substrate scope and mild conditions.

Keywords: C(sp3)-O bond formation; amino ferrocenes; aza-Michael addition; benzodihydrooxazole; catalyst-free.

Abstract

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