A Novel Synthesis of 4-Acetoxyl 5(4H)-Oxazolones by Direct α-Oxidation of N-Benzoyl Amino-Acid Using Hypervalent Iodine

Gang Wen; Wen-Xuan Zhang; Song Wu

doi:10.3390/molecules22071102

A Novel Synthesis of 4-Acetoxyl 5(4H)-Oxazolones by Direct α-Oxidation of N-Benzoyl Amino-Acid Using Hypervalent Iodine

Molecules. 2017 Jul 3;22(7):1102. doi: 10.3390/molecules22071102.

Authors

Gang Wen¹, Wen-Xuan Zhang², Song Wu³

Affiliations

¹ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China. wengang@imm.ac.cn.
² State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China. wxzhang@imm.ac.cn.
³ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China. ws@imm.ac.cn.

Abstract

We have developed a new method to prepare 4-acetoxy substituted 5(4H)-oxazolones by direct oxidation of N-benzoyl amino-acids using hypervalent iodine. The method is efficient, economical and easy to perform for the synthesis of quaternary substituted amino acid derivatives. We used online FTIR monitoring techniques to analyze the reaction, and gave a plausible reaction mechanism.

Keywords: 4-acetoxyl 5(4H)-oxazolones; N-benzoyl amino-acid; hypervalent iodine; online FTIR; oxidation.

Publication types

Letter

MeSH terms

Amino Acids / chemistry*
Catalysis
Iodine / chemistry*
Molecular Structure
Oxazolone / chemistry*
Oxidation-Reduction

Substances

Amino Acids
Oxazolone
Iodine