Categories: Synthesis of N-Heterocycles, Synthesis of O-Heterocycles > benzo-fused N-Heterocycles, benzo-fused O-Heterocycles >
Synthesis of Benzisoxazoles
Recent Literature
An efficient and facile PPh3-mediated Barbier-Grignard-type reaction
provides various 3-aryl or alkyl substituted 1,2-benzisoxazoles from
2-hydroxybenzonitriles and bromides in good yields.
G. Chen, H. Liu, S. Li, Y. Tang, P. Lu, K. Xu, Y. Zhang, Org. Lett.,
2017, 19, 1792-1795.
Various substituted benzisoxazoles have been prepared by a [3 + 2] cycloaddition
of nitrile oxides and arynes. Both highly reactive intermediates, have been
generated in situ by fluoride anion from readily prepared aryne precursors and
chlorooximes. The reaction scope is quite general, affording a novel, direct
route to functionalized benzisoxazoles under mild reaction conditions.
A. V. Dubrovskiy, R. C. Larock., 2010,
12, 1180-1183.
A divergent and regioselective synthesis of either 3-substituted benzisoxazoles
or 2-substituted benzoxazoles from readily accessible ortho-hydroxyaryl
N-H ketimines proceeds in two distinct pathways through a common N-Cl imine
intermediate: (a) N-O bond formation to form benzisoxazole under anhydrous
conditions and (b) NaOCl mediated Beckmann-type rearrangement to form
benzoxazole, respectively.
C.-y Chen, T. Andreani, H. Li, Org. Lett., 2011,
13, 6300-6303.