Citation: Mehdi Adib, Bagher Mohammadi, Ehsan Sheikhi, Hamid Reza Bijanzadeh. 1-Methylimidazole-catalyzed reaction between tosylmethyl isocyanide and dialkyl acetylenedicarboxylates:An efficient synthesis of functionalized pyrroles[J]. Chinese Chemical Letters, ;2011, 22(3): 314-317. doi: 10.1016/j.cclet.2010.10.032 shu

1-Methylimidazole-catalyzed reaction between tosylmethyl isocyanide and dialkyl acetylenedicarboxylates:An efficient synthesis of functionalized pyrroles

a School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran;
b Department of Chemistry, Tarbiat Modarres University, PO Box 14115-175, Tehran, Iran

Received Date: 29 June 2010

Fund Project: This research was supported by the Research Council of the University of Tehran as research project (No. 6102036/ 1/03).

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.
- 1-Methylimidazole,
- Tosylmethyl isocyanide,
- Acetylenic esters,
- Pyrrole synthesis
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