Copper-mediated synthesis of N-fused heterocycles via Csp–S coupling reaction and 5-endo-dig cyclization sequence

Dongmei Xiao; Liqiang Han; Qi Sun; Qianxi Chen; Ningbo Gong; Yang Lv; Franck Suzenet; Gerald Guillaumet; Tieming Cheng; Runtao Li

doi:10.1039/C2RA20254A

Copper-mediated synthesis of N-fused heterocycles via C_sp–S coupling reaction and 5-endo-digcyclization sequence†

Dongmei Xiao,^a Liqiang Han,^a Qi Sun,*^a Qianxi Chen,^b Ningbo Gong,^b Yang Lv,^b Franck Suzenet,^c Gerald Guillaumet,^c Tieming Cheng^a and Runtao Li*^a

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* Corresponding authors

^a State Key Laboratory of Natural and Biomimetic Drugs; School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing, China
E-mail: sunqi@bjmu.edu.cn
Fax: +86 (10)8271 6956
Tel: +86 (10)8280 1504

^b Institute of Materia Medica (IMM), Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, China

^c Institut de Chimie Organique et Analytique, Université d'Orléans, UMR-CNRS, rue de Chartres, BP 6759, 45067 Orléans cedex 2, France

Abstract

A novel method was developed for the preparation of N-fused heterocycles via a C_sp–S coupling reaction and a sequence of 5-endo-dig cyclization. This method involves the reaction of –NHC(S)NH-containing compounds and alkynes in the presence of CuCl and N,N′-dicyclohexylimidazolium chloride.

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Copper-mediated synthesis of N-fused heterocycles via C_sp–S coupling reaction and 5-endo-digcyclization sequence†

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Copper-mediated synthesis of N-fused heterocycles via C_sp–S coupling reaction and 5-endo-dig cyclization sequence

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RSC Advances

Copper-mediated synthesis of N-fused heterocycles via Csp–S coupling reaction and 5-endo-digcyclization sequence†

Abstract

Supplementary files

Article information

Download Citation

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Copper-mediated synthesis of N-fused heterocycles via Csp–S coupling reaction and 5-endo-dig cyclization sequence

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Copper-mediated synthesis of N-fused heterocycles via C_sp–S coupling reaction and 5-endo-digcyclization sequence†

Copper-mediated synthesis of N-fused heterocycles via C_sp–S coupling reaction and 5-endo-dig cyclization sequence