Categories: Synthesis of N-Heterocycles, Synthesis of O-Heterocycles > benzo-fused N-Heterocycles, benzo-fused O-Heterocycles >

Synthesis of 2,1-Benzisoxazoles

Recent Literature

Iron(II) bromide catalyzes the transformation of aryl and vinyl azides with ketone or methyl oxime substituents into 2,1-benzisoxazoles, indazoles, or pyrazoles through the formation of an N-O or N-N bond. This transformation tolerates various functional groups and facilitates access to a range of benzisoxazoles or indazoles.
B. J. Stokes, C. V. Vogel, L. K. Urnezis, M. Pan, T. G. Driver, Org. Lett., 2010, 12, 2884-2887.

An electrochemically mediated method enables the preparation of 2,1-benzisoxazoles from o-nitrophenylacetylenes. Different from the traditional electrochemical reduction of nitro to nitroso, the nitro group directly underwent a cyclization reaction with the alkyne activated by selenium cation generated by the anodic oxidation of diphenyl diselenide and finally produced the desired products.
L.-W. Wang, Y.-F. Feng, H.-M. Lin, H.-T. Tang, Y.-M. Pan, J. Org. Chem., 2021, 86, 16121-16127.