Facile synthesis of 1,4-oxazines by ruthenium-catalyzed tandem N-H insertion/cyclization of α-arylamino ketones and diazo pyruvates

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 RuCl 3 through a tandem N-H insertion/cyclization sequence via an enol formation...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-03, Vol.19 (8), p.1769-1772
Main Authors: Sajjad, Farrukh, Chen, Yanmei, Tian, Xue, Dong, Suzhen, Gopi Krishna Reddy, Alavala, Hu, Wenhao, Xing, Dong
Format: Article
Language:English
Subjects:
Anticancer properties
Chemical synthesis
Functional groups
Insertion
Ketones
Nucleotide sequence
Oxazine
Pyruvates
Ruthenium
Ruthenium trichloride
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Summary: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 RuCl 3 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. A RuCl 3 -catalyzed tandem N-H insertion/cyclization sequence from simple α-amino ketones and diazo pyruvates is realized, resulting a series of substituted 1,4-oxazines that show promising anticancer activities toward HCT116.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob01913e