208583-34-0Relevant academic research and scientific papers
Arylsulfonylpyrroles from reaction of tosylmethyl isocyanide (tosmic) with 3-arylsulfonyl acrylates as michael acceptors
Di Santo, Roberto,Costi, Roberta,Massa, Silvio,Artico, Marino
, p. 1801 - 1815 (2007/10/03)
Ethyl 3-(arylthio)acrylates did not react with α-alkali metalated tosylmethyl isocyanide (TosMIC) to afford 4-(arylthio)pyrrole-3-carboxylic acid ethyl esters. Oxidation of thioethers to sulfones generated reactive 3- (arylsulfonyl) acrylates, which promptly underwent cycloaddition with TosMIC in the presence of base giving ethyl 4-(arylsulfonyl)pyrrole-3-carboxylates. Contrary to expectation, the use of ethyl 3-(5-chloro-2- nitrophenylsulfonyl)acrylate led to ethyl ester of 5-tosylpyrrole-3- carboxylic acid instead of the expected ethyl 4-(5-chloro-2- nitrophenylsulfonyl)pyrrole-3-carboxylate.
