73403-03-9Relevant academic research and scientific papers
One-step synthesis of dialkyl 2-[(4-methylphenyl)sulfonyl]-1H-pyrrole-3,4- dicarboxylates by reaction of acetylenedicarboxylates with 'tosylmethyl isocyanide' (TsMIC) and triphenylphosphine
Alizadeh, Abdolali,Masrouri, Hassan,Rostamnia, Sadegh,Movahedi, Farnaz
, p. 923 - 926 (2006)
The reactive 1:1 adducts in the reaction between Ph3P and dialkyl acetylenedicarboxylates have been trapped with 'tosylmethyl isocyanide' (TsMIC; 1) to yield dialkyl 2-[(4-methylphenyl)sulfonyl]-1H-pyrrole-3,4- dicarboxylates 3 (Scheme 1). The
1-methylimidazole-catalyzed reaction between tosylmethyl isocyanide and dialkyl acetylenedicarboxylates: An efficient synthesis of functionalized pyrroles
Adib, Mehdi,Mohammadi, Bagher,Sheikhi, Ehsan,Bijanzadeh, Hamid Reza
, p. 314 - 317 (2011)
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 acetylenedicarboxylate
Development of a Synthetic Method for Multifunctionalized Pyrroles Using Isocyanide Dichloride as a Key Intermediate
Soeta, Takahiro,Matsumoto, Akihiro,Ukaji, Yutaka
, p. 4831 - 4834 (2018/04/26)
Multifunctionalized pyrrole derivatives were synthesized using a highly efficient method based on the Michael addition of carbanions generated in situ from isocyanide dichloride to α,β-unsaturated carbonyl compounds. The reactions proceeded smoothly to afford the pyrrole derivatives in good to high yields. A wide range of Michael acceptors, such as α,β-unsaturated carbonyl compounds and nitroolefin, were successfully applied to this reaction.
Base Mediated Reactions in Solid-Liquid Media. A 1,3-Dipolar Cycloaddition Route to Pyrrolines and Pyrroles from Imino Chlorosulfides.
Berree, Fabienne,Marchand, Evelyne,Morel, Georges
, p. 6155 - 6158 (2007/10/02)
Nitrile ylides, generated in basic conditions (HCl abstraction) from N- and N-imino chlorosulfides, undergo 1,3-dipolar cycloadditions with electron-deficient dipolarophiles to produce pyrroles and pyrrolines.Heterogeneous media are found to furnish the best conditions for these reactions.One pyrrole can also be prepared from methyl N- chlorothioimidate and dimethyl acetylenedicarboxylate on alumina-potassium fluoride mixture as solid support, under microwave irradiation. Key words: Imino chlorosulfides; alumina-dispersed potassium fluoride and potassium hydroxide; 1,3-dipolar cycloaddition; pyrroles.
