Palladium-Catalyzed Intermolecular Domino Reaction of gem-Dibromo­enynes with Anilines; A One-Pot Synthesis of Quinolines and Quinolinones

Tianhao Meng; Wen-Xiong Zhang; Hui-Jun Zhang; Yun Liang; Zhenfeng Xi

doi:10.1055/s-0032-1316613

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(17): 2754-2762
DOI: 10.1055/s-0032-1316613

paper

Palladium-Catalyzed Intermolecular Domino Reaction of gem-Dibromoenynes with Anilines; A One-Pot Synthesis of Quinolines and Quinolinones

Tianhao Meng

^aBeijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190, P. R. of China

,

Wen-Xiong Zhang

^bBeijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China, Fax: +86(10)62759728 eMail: zfxi@pku.edu.cn

,

Hui-Jun Zhang

^bBeijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China, Fax: +86(10)62759728 eMail: zfxi@pku.edu.cn

,

Yun Liang

^bBeijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China, Fax: +86(10)62759728 eMail: zfxi@pku.edu.cn

,

Zhenfeng Xi*

^bBeijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China, Fax: +86(10)62759728 eMail: zfxi@pku.edu.cn

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Abstract

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Abstract

An efficient domino process involving palladium-catalyzed amination of an alkenyl bromide, 1,5-H transfer, annulation via 6-exo-dig electrophilic cyclization, and palladium-catalyzed etherification, is described. This reaction provides an efficient one-pot synthesis of multi-substituted quinolines and quinolinones from gem-dibromoenynes and anilines.

Key words

alkenes - enynes - etherification - quinoline - quinolinone

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Referenzen

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Zusatzmaterial

Supporting Information

Palladium-Catalyzed Intermolecular Domino Reaction of gem-Dibromo­enynes with Anilines; A One-Pot Synthesis of Quinolines and Quinolinones

Palladium-Catalyzed Intermolecular Domino Reaction of gem-Dibromoenynes with Anilines; A One-Pot Synthesis of Quinolines and Quinolinones