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Phosphine-Mediated Morita-Baylis-Hillman-Type/Wittig Cascade: Access to E-Configured 3-Styryl- and 3-(Benzopyrrole/furan-2-yl) Quinolinones.
Zheng, Yu; Wang, Zhi-Wei; Cheng, Wen-Shuo; Xie, Zhen-Zhen; He, Xian-Chen; Chen, Yan-Shan; Chen, Kai; Xiang, Hao-Yue; Chen, Xiao-Qing; Yang, Hua.
  • Zheng Y; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
  • Wang ZW; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
  • Cheng WS; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
  • Xie ZZ; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
  • He XC; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
  • Chen YS; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
  • Chen K; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
  • Xiang HY; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
  • Chen XQ; School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, Henan, P. R. China.
  • Yang H; College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
J Org Chem ; 87(2): 974-984, 2022 01 21.
Article en En | MEDLINE | ID: mdl-34985275
ABSTRACT
A phosphine-mediated, well-designed Morita-Baylis-Hillman-type/Wittig cascade for the rapid assembly of a quinolinone framework from benzaldehyde derivatives is developed for the first time. By rationally combining I2/NIS-mediated cyclization, biologically relevant 3-(benzopyrrole/furan-2-yl) quinolinones were facilely synthesized in a one-pot process by starting from 3-styryl-quinolinones bearing an o-hydroxy/amino group, significantly expanding the chemical space of this privileged skeleton. Further utility of this protocol is illustrated by successfully performing this transformation in a catalytic manner through in situ reduction of phosphine oxide by phenylsilane.
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Texto completo: 1 Banco de datos: MEDLINE Asunto principal: Fosfinas / Quinolonas Idioma: En Año: 2022 Tipo del documento: Article
Texto completo
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XML
PubMed Links
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Texto completo: 1 Banco de datos: MEDLINE Asunto principal: Fosfinas / Quinolonas Idioma: En Año: 2022 Tipo del documento: Article