100461-51-6

Upstream product

• 124530-80-9 N-acetyl-2-(2-aminophenylthio)indan-1-one 
• 95-13-6 1-indene 
• 7669-54-7 2-nitrobenzenesulfenyl chloride 
• 124530-81-0 N-Acetyl-2-(2-aminophenylthio)indan-1-ol 

Relevant academic research and scientific papers

Reaction of 2,2'-Dithiodianiline with 2-Alkyl-1,3-diketones. Synthesis and Chemical Behaviour of Some 2-Acyl-2H-1,4-benzothiazines

The reactions of 2,2'-dithiodianiline 1 with 2-alkyl-1,3-diketones 2a-d have been employed in order to synthesize 2-acyl-2H-1,4-benzothiazines.In the cases of 2a,b the expected 2-acyl-2H-1,4-benzothiazines, i.e. 3a,b were obtained, whereas the reactions of 1 with the 1,3-diketones 2c,d afforded the α-ketosulfide 12 and the 1,4-benzothiazine 17, respectively.The products 3a,b underwent the hydrolytic C2-C3 bond cleavage of the thiazine nucleus to give the α-ketosulfides 6 and 11, respectively.Such an hydrolytic process explains the formation of the compound 12in the reaction of 1 with 2c.The formation of 17 in the case of 2d is considered to be formed through a rearrangement involving the 1,3-sulfur shift of the preformed 1,4-benzothiazine 3d.

SYNTHESIS AND REACTIONS OF TRANS-2-(2'-NITROPHENYLTHIO)-1-CHLOROINDANE

The title compound was prepared by addition of 2-nitrobenzenesulphenyl chloride to indene, and proton nmr was used to prove its trans-structure.The chloro-substituent could be replaced by ethanol under very mild conditions with retention of configuration owing to anchimeric assistance by the bridging S-atom.Analogous reactions were observed with water and other alcohols (MeOH, Me2CHOH, Me3COH, PhSH).Basic nucleophiles caused dehydro-chlorination to the corresponding indenes.Reduction of the nitro-group resulted in intramolecular cyclisation to give a dihydrobenzindenothiazine 9.Thermolysis of the 2-(2'-nitrophenylthio)-1-azidoindane occurred with ring expansion to give 3-(2'-nitrophenylthio)quinoline.Oxidation of the title compound with m-chloroperoxybenzoic acid produced the corresponding sulphone which smoothly underwent reductive cyclisation to a benzindenothiazinesulphone 20.