121006-80-2

Upstream product

• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 4553-11-1 2-(5-bromo-2,3-dihydro-2-oxo-1H-indol-3-ylidene)hydrazinecarbothioamide 
• 536-38-9 4-chlorobenzoylmethyl bromide 

Downstream Products

• 121006-88-0 1-(p-Chlorophenyl)-7-bromothiazolo<2',3':3,4><1,2,4>triazino<5,6-b>indole 

Relevant academic research and scientific papers

Heterocyclic systems containing bridgehead nitrogen atom : Part LXXII - Reaction of 5H-2,3-dihydro-1,2,4-triazinoindole-3-thiones with phenacyl bromide, 1,2-dibromomethane and chloroacetic acid

8-Bromo-5H-dihydro-1,2,4-triazinoindole-3-thione (III), obtained by the reaction of 5-bromoisatin (I) with thiosemicarbazide followed by cyclization of the intermediate 5-bromoisatin-3-thiosemicarbazone (II) with alkali, on condensation with phenacyl bromide gives 8-bromo-3-phenacylthio-5H-1,2,4-triazinoindole (IV).The ketone IV on polyphosphoric acid-catalyzed cyclization furnishes 7-bromo-3-phenylthiazolotriazinoindole (Va) and not 7-bromo-1-phenylthiazolotriazinoindole (VIIa) which has been obtained through unequivocal synthesis.The reaction of III with 1,2-dibromoethane, on the other hand, yields7-bromo-1,2-dihydrothiazolotriazinoindole (VIII), identical with the authentic compound obtained by the reaction II with 1,2-dibromoethane. 5H-6-Methyl-1,2,4-triazinoindole-3-thiolacetic acid (XI), obtained by the reacvtion of 5H-2,3-dihydro-6-methyl-1,2,4-triazinoindole-3-thione (X) with chloroacetic acid, on cyclization with acetc anhydride in the presence or absence of pyridine gave 2-acetyl-3-hydroxy-9-methylthiazolotriazinoindole (XIII).All structures have been established by IR, 1H NMR and mass spectral data.

Heterocyclic Systems Containing Bridgehead Nitrogen Atom: Synthesis of Thiazolotriazinoindoles and Isomeric Thiazolotriazinoindoles

8-Bromo- and 7-chloro-5H-2,3-dihydrotriazinoindole-3-thiones (II) on condensation with α-halogenoketones give 5H-3-aroylmethylthio-8-bromo- and 5H-3-aroylmethylthio-7-chlorotriazinoindole hydrohalides (III) which undergo PPA cyclization to furnish 3-aryl-7-bromo- and 3-aryl-8-chloro-thiazolotriazinoindoles (IV) and not the angular isomeric 1-aryl-7-bromo- and 1-aryl-8-chloro-thiazolotriazinoindoles (VI).The unequivocal synthesis of the latter (VI) has also been accomplished.