Synthesis and analgesic activity of some 1-benzofurans, 1-benzothiophenes and indoles

3-Unsubstituted 1-benzofurans 1e and 1f, 3-methyl-1-benzofurans 1a-1d, and 3-amino-1-benzofurans 2a-2l, as well as 3-amino-1-benzothiophenes aa, 3b an d 3-aminoindoles 4a-4f 11a, and 11b were prepared and tested as analgesics. The 3-amino-1-benzofurans 2 were prepared from the corresponding 2-hydroxy benzonitriles 5 and phenacyl bromides 6 via intermediates 7. Similar treatm ent df 2-sulfanlylbenzonitrile (8) provided 3-amino-1-benzothiophenes 3. ap propriately substituted 2-aminobenzonitriles 9 then provided N-substituted 3-aminoindoles 4. 1-(Ethoxycarbonyl)indoles 4e and 4f were successfully dep rotected giving indoles 11a and 11b, respectively.