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 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.

Citation

Farrukh Sajjad, Yanmei Chen, Xue Tian, Suzhen Dong, Alavala Gopi Krishna Reddy, Wenhao Hu, Dong Xing. Facile synthesis of 1,4-oxazines by ruthenium-catalyzed tandem N-H insertion/cyclization of α-arylamino ketones and diazo pyruvates. Organic & biomolecular chemistry. 2021 Mar 04;19(8):1769-1772

PMID: 33538720

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