Microwave-promoted synthesis of 3-amino-substituted 1,2-benzisoxazoles
2010
Background: 1,2-benzisoxazole derivatives have been the focus of numerous studies, due to their biological and chemical interest. Results: We demonstrate an efficient synthesis of a series of 3-amino-substituted 1,2-benzisoxazoles from a 3-chloro-1,2-benzisoxazole by microwave-promoted nucleophilic aromatic substitution. The 3-amino-1,2-benzisoxazoles prepared were obtained in 1–6 h in good-to-high yields of 54–90%. The 3-chloro-1,2-benzisoxazoles were also prepared by heating with microwave irradiation in quantitative yields in 2 h, from the corresponding 3-hydroxy-1,2-benzisoxazoles. Conclusion: This efficient microwave-assisted pathway could be applied to a variety of substrates in the further development of substituted 1,2-benzisoxazoles.
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