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CCC pincer Ru complex-catalyzed C-H vinylation/6π-E-cyclization of aldimines for constructing 4H-pyrido[1,2-a]pyrimidines.
Cai, Heng; Tu, Yong-Qiang; Niu, Qiang; Xie, Wen-Ping; Wang, Bin; Lu, Ka; Li, Zi-Hao; Zhang, Fu-Min; Zhang, Xiao-Ming.
Afiliación
  • Cai H; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University Lanzhou 730000 P. R. China tuyq@lzu.edu.cn.
  • Tu YQ; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University Lanzhou 730000 P. R. China tuyq@lzu.edu.cn.
  • Niu Q; School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University Shanghai 200240 P. R. China tuyq@sjtu.edu.cn.
  • Xie WP; National Enterprise Technology Center, Inner Mongolia Erdos Electric Power and Metallurgy Group Co., Ltd Ordos 016064 Inner Mongolia China.
  • Wang B; School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University Shanghai 200240 P. R. China tuyq@sjtu.edu.cn.
  • Lu K; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University Lanzhou 730000 P. R. China tuyq@lzu.edu.cn.
  • Li ZH; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University Lanzhou 730000 P. R. China tuyq@lzu.edu.cn.
  • Zhang FM; School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University Shanghai 200240 P. R. China tuyq@sjtu.edu.cn.
  • Zhang XM; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University Lanzhou 730000 P. R. China tuyq@lzu.edu.cn.
Chem Sci ; 2024 Sep 03.
Article en En | MEDLINE | ID: mdl-39296994
ABSTRACT
An unusual cascade C-H activation, vinylation and 6π-electrocyclization of 2-pyridyl aldimines with vinyl bromides/triflates was achieved using catalysis with a unique CCC pincer NHC-Ru(iii) complex (Cat B). This reaction was found to enable a rapid and diverse synthesis of polycyclic 4H-pyrido[1,2-a]pyrimidine derivatives in mostly good to high yields, and with a broad substrate scope. A mechanistic study suggested the formation of a semi-opened Ru(iii) intermediate chelating/activating the aldimine, and the occurrence of single-electron transfer (SET) to generate a vinyl radical, followed by vinylation and then an intramolecular 6π-electrocyclization of 1N,3N-hexatrene to form the product. This protocol provides a convenient approach for preparing and seeking new drug candidates.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2024 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2024 Tipo del documento: Article Pais de publicación: Reino Unido