SYNTHESIS OF THIOAPLYSINOPSIN ANALOGS DERIVED FROM 5-DIMETHYLAMINOMETHYLIDENE-2-THIOXO-1,3-THIAZOL-4-ONES

摘要

Some new thioaplysinopsin analogs 4a-d were prepared from indole (3a) and or 2-methylindole (3b) and 5-dimethylaminomethylidene- (2a-c) or 5-ethoxymethylidene-2-thioxo-l,3-thiazol-4-ones (2d) derived rhodanine derivatives (la,b).Cycloaddition of N-phenyl-4-chlorobenzonitrileimine to C=S bond in 4c and in thioaplysinopsin derivatives 6a,b afforded the corresponding spiro compounds 4,9-diphenyl-2-(4-chlorophenyl)-7-[1-(2-methylindol-3-yl)methylidene]-l,6-dithia-3,4,9-triazaspiro-[4.4]non-2-en-8-one (5) and 2-(4-chlorophenyl)-8-[(Z)-1-(2-methyl- 1H-indol-3-yl)methylidene]-4,6-diaryl-1 -thia-3,4,6,9-tetraazaspiro[4.4]non-3-en-7-one (7a,b).