Abstract
The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C-C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)2/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated.
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Mikhaylov, A. A., Dilman, A. D., Novikov, R. A., Khoroshutina, Y. A., Struchkova, M. I., Arkhipov, D. E., … Ioffe, S. L. (2016). Tandem Pd-catalyzed C-C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes. Tetrahedron Letters, 57(1), 11–14. https://doi.org/10.1016/j.tetlet.2015.10.091
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