516448-22-9Relevant academic research and scientific papers
Part 1: Synthesis of polyfused heterocyclic systems derived from 3-phenyl-5,6,7,8-tetrahydro[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazepine-6,8- dione
Abd Allah
, p. 2871 - 2881 (2002)
3-Phenyl-5,6,7,8-tetrahydro[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine-6,8- dione (1) was condensed with o-aminothiophenol, 2-amino-ethanol or cystamine to afford compounds 2-4 respectively. Treatment of compound 1 with dimethylthiomethylenemalononitrile yielded the corresponding pyrano[3,2-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine derivative 5. 7-[5-Amino-1,3-dithiolan-2-ylidene]-3-phenyl-5,6,7,8-tetrahydro[1,2,4] triazolo[3,4-b][1,3,4]thiadiazepine-6,8-dione (6) was obtained by treating compound 1 with CS2 and chloroacetonitrile. Thiation of compound 1 gave the corresponding thioanalog 7, which in turn was condensed with malononitrile to give 3-phenyl-5,6,7,8-tetrahydro[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine-6-one- 8-ylidenemalononitrile (8). On treating compound 8 with benzaldehyde or p-nitrobenzaldehyde, pyrano[1,2,4]triazolo[1,3,4]thiadiazepin derivatives 9a,b, respectively, were obtained. Compound 8 was treated with CS2 and methyl iodid to give the corresponding dithiomethyl-methylene derivative 10 which was subjected to react with aniline to give pyrido[1,2,4]triazolo[1,3,4]thiadiazepine derivative 11. Compound 8 was treated with 3-aminopyridine, o-aminothiophenol, or o-phenylenediamene to yield compounds 12 and 13a,b respectively. Finally, tertiary amines or activated phenols were condensed with compound 8 to yield compounds 14 and 15a,b respectively.
