Your browser doesn't support javascript.
loading
Boronic-Acid-Accelerated Electrophilic Activation of Unprotected Maltols to N-Substituted Hydroxypyridinones in Water.
Ke, Di; Zhang, Lei; Zhong, Xiuwen; Shao, Jiaan; Yu, Yongping; Chen, Wenteng.
Afiliación
  • Ke D; College of Pharmaceutical Sciences, Zhejiang University, Zhejiang, Hangzhou 310058, People's Republic of China.
  • Zhang L; College of Pharmaceutical Sciences, Zhejiang University, Zhejiang, Hangzhou 310058, People's Republic of China.
  • Zhong X; College of Pharmaceutical Sciences, Zhejiang University, Zhejiang, Hangzhou 310058, People's Republic of China.
  • Shao J; School of Medicine, Zhejiang University City College, Zhejiang, Hangzhou 310015, People's Republic of China.
  • Yu Y; College of Pharmaceutical Sciences, Zhejiang University, Zhejiang, Hangzhou 310058, People's Republic of China.
  • Chen W; College of Pharmaceutical Sciences, Zhejiang University, Zhejiang, Hangzhou 310058, People's Republic of China.
Org Lett ; 24(6): 1263-1267, 2022 02 18.
Article en En | MEDLINE | ID: mdl-35124962
3,4-Hydroxypyridinone (3,4-HOPO) is a vital metal-chelating pharmacophore. However, the efficient synthesis has been a long-standing problem in drug development. In this paper, we report an efficient electrophilic activation of unprotected maltols via reversible covalent bonds between boronic acid and 3-hydroxyl/4-carbonyl. This one-pot reaction proceeded well on a gram scale in water with excellent efficiencies up to 97%. Moreover, taking advantage of the covalent interactions via the transient boronate, most of the previously tough amine donors, including sterically hindered amines, aromatic amines, and amino acids and amino alcohols, were well-tolerated. Importantly, the potential of this strategy in the pharmaceutical industry was highlighted with a successful synthesis of 3,4-HOPOs containing iron-chelating active pharmaceutical ingredients on 10 g and kilogram scales.
Asunto(s)
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Piridonas / Pironas / Ácidos Borónicos / Agua Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2022 Tipo del documento: Article Pais de publicación: Estados Unidos
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Piridonas / Pironas / Ácidos Borónicos / Agua Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2022 Tipo del documento: Article Pais de publicación: Estados Unidos