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Facile synthesis of 1,4-oxazines by ruthenium-catalyzed tandem N-H insertion/cyclization of α-arylamino ketones and diazo pyruvates.
Sajjad, Farrukh; Chen, Yanmei; Tian, Xue; Dong, Suzhen; Gopi Krishna Reddy, Alavala; Hu, Wenhao; Xing, Dong.
Affiliation
  • Sajjad F; Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Rd., Shanghai, 200062, China. dxing@sat.ecnu.edu.cn.
  • Chen Y; Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Rd., Shanghai, 200062, China. dxing@sat.ecnu.edu.cn.
  • Tian X; A School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China. huwh9@mail.sysu.edu.cn.
  • Dong S; Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Rd., Shanghai, 200062, China. dxing@sat.ecnu.edu.cn.
  • Gopi Krishna Reddy A; A School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China. huwh9@mail.sysu.edu.cn.
  • Hu W; Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Rd., Shanghai, 200062, China. dxing@sat.ecnu.edu.cn and A School of Pharmaceutical Sciences, Sun Yat-sen Universi
  • Xing D; Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Rd., Shanghai, 200062, China. dxing@sat.ecnu.edu.cn.
Org Biomol Chem ; 19(8): 1769-1772, 2021 03 04.
Article in En | MEDLINE | ID: mdl-33538720
ABSTRACT
Herein, we report an efficient strategy for the rapid construction of 1,4-oxazines starting from simple α-amino ketones and diazo pyruvates under mild reaction conditions. This transformation is efficiently catalyzed by RuCl3 through a tandem N-H insertion/cyclization sequence via an enol formation. This reaction shows broad functional group tolerance, and the resulting 1,4-oxazine products show promising anticancer activities toward HCT116.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2021 Document type: Article Affiliation country: China
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2021 Document type: Article Affiliation country: China