Synthesis 2014; 46(24): 3356-3364
DOI: 10.1055/s-0034-1379045
paper
© Georg Thieme Verlag Stuttgart · New York

A Catalyst System, Copper/N-Methoxy-1H-pyrrole-2-carboxamide, for the Synthesis of Phenothiazines in Poly(ethylene glycol)

Manna Huang
a   School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, P. R. of China   Fax: +86(20)84113610   Email: ceswyq@mail.sysu.edu.cn
,
Jianying Hou
a   School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, P. R. of China   Fax: +86(20)84113610   Email: ceswyq@mail.sysu.edu.cn
,
Ruiqiao Yang
b   Hunan College for Preschool Education, Changde 415000, P. R. of China
,
Liting Zhang
a   School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, P. R. of China   Fax: +86(20)84113610   Email: ceswyq@mail.sysu.edu.cn
,
Xinhai Zhu*
a   School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, P. R. of China   Fax: +86(20)84113610   Email: ceswyq@mail.sysu.edu.cn
,
Yiqian Wan*
a   School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, P. R. of China   Fax: +86(20)84113610   Email: ceswyq@mail.sysu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 01 July 2014

Accepted after revision: 06 August 2014

Publication Date:
10 September 2014 (online)


Abstract

A copper/N-methoxy-1H-pyrrole-2-carboxamide catalyst system has been established for the preparation of phenothiazines in good yields by two routes, starting from 2-iodoanilines and 2-bromobenzenethiol and from aryl ortho-dihalides and o-aminobenzenethiols, by conducting the reaction at 90 °C in poly(ethylene glycol)-100 (PEG-100). In addition, the catalyst system was useful for promoting direct arylation of various aryl amines, aliphatic amines, and aqueous ammonia. The simple experimental operation, low loading of catalyst system together with the use of green solvent, makes it attractive for the versatile syntheses of phenothiazines and various amines.

Supporting Information

 
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