Synthesis of 6-Hydroxy-1,2-benzisoxazoles 3a-f (General Method). A stirred solution of oxime 2a-f
(10 mmol) in anhydrous THF (20 ml) was cooled (20-25°С) and treated by addition of 1,1'-carbonyldiimidazole
(3.24 g, 20 mmol). The reaction mixture was stirred for 2-3 h at room temperature, then for 1-4 h at 40-50°С,
the solvent was evaporated under vacuum; the residue was transferred into cold water (100 ml), the precipitate
formed was filtered off and recrystallized from МеОН.
6-Hydroxy-3-phenyl-1,2-benzisoxazole (3а). Yield 1.50 g (71%). Colorless crystals, mp 217-219°С
(mp 218-219°С [10]).
Synthesis of 7-(Aminomethyl)-6-hydroxy-1,2-benzisoxazoles 4a-h (General Method). A hot solution
of 6-hydroxy-1,2-benzisoxazole 3b,d-f (1.0 mmol) in anhydrous EtOH (10 ml) was treated by addition of the
corresponding aminal (1.2 mmol); the mixture was refluxed for 3-5 h, then cooled. The solvent was removed by
evaporation under vacuum, the residue was recrystallized from hexane.
Synthesis of 7-(Aminomethyl)-6-hydroxy-1,2-benzisoxazoles 4i-m (General Method). A hot solution
of 6-hydroxy-1,2-benzisoxazole 3a,с,d,f (1.0 mmol) in anhydrous EtOH (10 ml) was treated by addition of
paraform (36 mg, 1.2 mmol) and 1-(2-pyridyl)piperazine (1.1 mmol) or the corresponding piperidinecarboxylic
acid. The reaction mixture was refluxed for 6-8 h, then cooled, solvent was evaporated under vacuum, the
residue was recrystallized from hexane or 1:2 mixture of 2-PrOH–hexane.
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