Synthesis of New Dioximes and Tetraoximes from Reaction of Aminothiophenoles with Dichloroglyoxime

Abstract

The reaction of 2-aminothiophenol with dichloroglyoxime in alkaline solution of MeOH led to (2E,3E)-2H- 1,4-benzothiazine-2,3(4H)dionedioxime (1). The compounds (2Z,6Z)-1,4-bis(2-mercaptophenyl)-piprazine-2,3,5,6- tetraone tetraoxime (2), (1Z,2Z)-N¹´,N²´-dihydroxy-N¹,N²- bis-(2-mercaptophenyl)ethanediimidamide (3), bis(2- aminophenyl) (1Z,2Z)-N¹,N²-dihydroxyethane bis-(imidothioate) (4) and 2-aminophenyl (1Z,2Z)-N-hydroxy-2-hydroxyimino- 2-[(2-mercaptophenyl)amino]ethanimidothioate (5), were obtained from the reaction of 1,2-aminothiophenol with dichloroglyoxime in different condition. The compounds (3, 4 and 5) can be converted to (1) in the presence of dichloroglyoxime. But, In the same condition compounds (3E,4E,11E, 12E)-2,10-dithia-5,13-diazatricyclo[12.2.2.2^6,9]icosa-1 (16),6,8,14,17,19-hexaene-3,4,11,12-tetraone tetraoxime (6a) and (3E,4E,12E, 13E)-2,11-dithia-5,14-diazatricyclo- [13.3.1.1^6,10]icosa-1(19), 6(20), 7,9,15,17-hexaene-3,4,12,13- tetraonetetraoxime (6b) were synthesized from the reaction of 1,4- and 1,3-aminothiophenol with dichloroglyoxime, respectively.