The reaction between ethyl 3-bromopyruvate and p-substituted anilines was found to involve the unexpected participation of acetone (solvent) forming N-aryl-5-methyl-pyrrole-3-carboxylates.The influence of p-substituen...The reaction between ethyl 3-bromopyruvate and p-substituted anilines was found to involve the unexpected participation of acetone (solvent) forming N-aryl-5-methyl-pyrrole-3-carboxylates.The influence of p-substituents of aniline and the feasibility with other ketones were studied.N-aryl-indole-3-carboxylate (17) was synthesized successfully with this method.The unique character of p-methoxy-aniline in this reaction was discussed.展开更多
An efficient 1-methylimidazole-catalyzed synthesis of dialkyl 2-[（4-methylphenyl）sulfonyl]-1H-pyrrole-3,4-dicarboxylates is described.The reactive 1：1 zwitterionic intermediate formed by the addition of 1-methylimi...An efficient 1-methylimidazole-catalyzed synthesis of dialkyl 2-[（4-methylphenyl）sulfonyl]-1H-pyrrole-3,4-dicarboxylates is described.The reactive 1：1 zwitterionic intermediate formed by the addition of 1-methylimidazole to dialkyl acetylenedicarboxylates is trapped by tosylmethyl isocyanide（TOSMIC） to afford the title compounds in excellent yields.展开更多
文摘The reaction between ethyl 3-bromopyruvate and p-substituted anilines was found to involve the unexpected participation of acetone (solvent) forming N-aryl-5-methyl-pyrrole-3-carboxylates.The influence of p-substituents of aniline and the feasibility with other ketones were studied.N-aryl-indole-3-carboxylate (17) was synthesized successfully with this method.The unique character of p-methoxy-aniline in this reaction was discussed.
基金supported by the Research Council of the University of Tehran as research project(No6102036/ 1/03)
文摘An efficient 1-methylimidazole-catalyzed synthesis of dialkyl 2-[（4-methylphenyl）sulfonyl]-1H-pyrrole-3,4-dicarboxylates is described.The reactive 1：1 zwitterionic intermediate formed by the addition of 1-methylimidazole to dialkyl acetylenedicarboxylates is trapped by tosylmethyl isocyanide（TOSMIC） to afford the title compounds in excellent yields.
