Abstract
3-Amidinomethyl- (8), 3-imidazolinylmethyl- (9) and 3-tetrahydropyrimidinylmethyl-1, 2-benzisoxazole (10) were synthesized from 1, 2-benzisoxazole-3-acetonitrile (4) via iminoether (7). 3-Tetrazolylmethyl-1, 2-benzisoxazole (5) and 1, 2-benzisoxazole-3-acetamide oxime (11) were also prepared from 4. 3-Aminoethyl-1, 2-benzisoxazole (25), a tryptamine analogue of 1, 2-benzisoxazole, was synthesized from 3-chloroethyl-1, 2-benzisoxazole (20). The bromination of 1, 2-benzisoxazole-3-acetic acid (1) with one molar equivalent of bromine afforded α-bromo-1, 2-benzisoxazole-3-acetic acid (27), which was decarboxylated to give 3-bromomethyl-1, 2-benzisoxazole (30). The amination of 30 afforded 3-amino-methyl-1, 2-benzisoxazole (31). The bromination of 1 with excess of bromine gave 3-tribromomethyl-1, 2-benzisoxazole (28). N-Substituted 1, 2-benzisoxazolylglycine ester (32) was synthesized from methyl α-bromo-1, 2-benzisoxazole-3-acetate (29) which was obtained by the bromination of methyl 1, 2-benzisoxazole-3-acetate (2).
