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

Manna Huang; Jianying Hou; Ruiqiao Yang; Liting Zhang; Xinhai Zhu; Yiqian Wan

doi:10.1055/s-0034-1379045

Synthesis, Table of Contents

Synthesis 2014; 46(24): 3356-3364
DOI: 10.1055/s-0034-1379045

paper

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

Manna Huang

^aSchool 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

^aSchool 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

^bHunan College for Preschool Education, Changde 415000, P. R. of China

,

Liting Zhang

^aSchool 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*

^aSchool 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*

^aSchool 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

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Abstract

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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.

Key words

copper - homogeneous catalysis - amination - green chemistry - heterocycles

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References

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