1452849-75-0

Upstream product

• 1452776-84-9 tert-butyl 2-(3-(methylsulfonyl)thioureido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 100-39-0 benzyl bromide 
• 207743-78-0 tert-butyl 2-isothiocyanato-4,5,6,7-tetrahydrobenzo[b]-thiophene-3-carboxylate 
• 92932-02-0 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid tert-butyl ester 

Downstream Products

• 1452849-80-7 (Z)-2-((methylsulfonamido)(benzylsulfanyl)methyleneamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid 
• 1452776-89-4 2-(benzylsulfanyl)-3-(methylsulfonyl)-5,6,7,8-tetrahydrobenzo-[4,5]thieno[2,3-d]pyrimidin-4(3H)-one 

Relevant academic research and scientific papers

Regioselective sulfonylation and N- to O-sulfonyl migration of quinazolin-4(3H)-ones and analogous thienopyrimidin-4(3H)-ones

The sulfonylation of quinazolin-4(3H)-ones and related tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-ones with mesyl, tosyl, and p-cyanobenzenesulfonyl chloride was studied. A hydrogen substituent at 2-position directed the sulfonyl group to the N-3 position, while alkylsulfanyl or amino substituents led to sulfonylation of the carbonyl oxygen. The latter effect was attributed to steric influence and the positive mesomeric effect of the 2-substituent. An access to N-sulfonylated 2-substituted regioisomers was established. An unexpected 1,3-sulfonyl migration was observed and further analyzed. This process occurred as an intramolecular N- to O-shift as verified by kinetic and crossover experiments.