Synthesis 2014; 46(09): 1167-1176
DOI: 10.1055/s-0033-1338606
paper
© Georg Thieme Verlag Stuttgart · New York

Cascade Reaction between Methyl 3-Dehydroshikimate, Arylamines, and 2-Chloroalkyl Esters under Microwave Conditions: A Practical and Biomass-Based Synthesis of N-Aryl-1,4-benzoxazin-3-ones

Ensheng Zhang
a   Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, P. R. of China   Fax: +86(20)85231119   Email: zouyong@gic.ac.cn
b   University of Chinese Academy of Sciences, Beijing, 100039, P. R. of China
,
Tianlong Xu
a   Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, P. R. of China   Fax: +86(20)85231119   Email: zouyong@gic.ac.cn
b   University of Chinese Academy of Sciences, Beijing, 100039, P. R. of China
,
Wen Wei
a   Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, P. R. of China   Fax: +86(20)85231119   Email: zouyong@gic.ac.cn
,
Tongkun Huang
a   Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, P. R. of China   Fax: +86(20)85231119   Email: zouyong@gic.ac.cn
,
Mu Yuan
c   Guangzhou Medical University, Guangzhou 510182, P. R. of China
,
Wei Zeng
d   School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, P. R. of China
,
Yong Zou*
a   Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, P. R. of China   Fax: +86(20)85231119   Email: zouyong@gic.ac.cn
c   Guangzhou Medical University, Guangzhou 510182, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 23 December 2013

Accepted after revision: 17 February 2014

Publication Date:
17 March 2014 (online)


Abstract

A biomass-based, metal- and ligand-free assembly of N-aryl-1,4-benzoxazin-3-ones from methyl 3-dehydroshikimate (3-MHDS), involving aliphatic to aromatic transformation followed by C–O and C–N forming reactions, is presented. A variety of N-aryl-1,4-benzoxazin-3-ones were efficiently synthesized in a one-pot consecutive manner under microwave conditions.

Supporting Information