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

doi:10.1016/j.cclet.2010.10.032

Cited by 19 publications

(8 citation statements)

References 21 publications

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“…In 2011, the Adib group developed a protocol that is different with respect to the common shortcomings such as long reaction time, low yield, expensive raw materials, and harsh reaction conditions. A mixture of TosMIC 16 , and a dialkyl acetylenedicarboxylate 138 , in the presence of a catalytic amount of 1-methylimidazole 139 undergoes a smooth addition reaction in anhydrous CH 2 Cl 2 at room temperature to afford 2,3,4-trisubstituted pyrroles 140 in yields of 90–95% ( Scheme 44 ) [ 63 ].…”

Section: Synthesis Of Pyrrole Derivatives By [3+2] Cycloaddition Omentioning

confidence: 99%

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Zhang

2018

Molecules

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Pyrrole and its polysubstituted derivatives are important five-membered heterocyclic compounds, which exist alone or as a core framework in many pharmaceutical and natural product structures, some of which have good biological activities. The Van Leusen [3+2] cycloaddition reaction based on tosylmethyl isocyanides (TosMICs) and electron-deficient compounds as a substrate, which has been continuously developed due to its advantages such as operationally simple, easily available starting materials, and broadly range of substrates, is one of the most convenient methods to synthetize pyrrole heterocycles. In this review, we discuss the different types of two carbon synthons in the Van Leusen pyrrole reaction and give a summary of the progress of these synthesis methods in the past two decades.

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Section: Synthesis Of Pyrrole Derivatives By [3+2] Cycloaddition Omentioning

confidence: 99%

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Zhang

2018

Molecules

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“…Given the influence of isocyanides in research front of synthesis of wide variety of heterocyclic systems, we also tried to provide more insight to isocyanide chemistry, including some reaction mechanisms and discussing their optimal reaction conditions. Isocyanide-based syntheses of pyrrole derivatives have been studied extensively [138][139][140][141][142][143][144][145] . Using Ag 2 CO 3 as catalyst, Lei et al developed an efficient, rapid and atom economy click-type synthetic method for preparing multi-substituted pyrroles 16.…”

Section: Introductionmentioning

confidence: 99%

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

2016

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“…electron decient alkenes, alkynes, ketene and dithioacetals. [22][23][24] However, the need for improving Van Leusen's pyrrole synthesis is evident. Subsequently, Adib and coworkers described an efficient and novel synthesis of dialkyl 2-[(4-methylphenyl)sulfonyl]-1Hpyrrole-3,4-dicarboxylates 4 by the reaction of dialkylacetylene dicarboxylates 3 with TosMIC 1a using 1-methylimidazole as a catalyst.…”

Section: Pyrrolesmentioning

confidence: 99%

“…Subsequently, Adib and coworkers described an efficient and novel synthesis of dialkyl 2-[(4-methylphenyl)sulfonyl]-1Hpyrrole-3,4-dicarboxylates 4 by the reaction of dialkylacetylene dicarboxylates 3 with TosMIC 1a using 1-methylimidazole as a catalyst. 23 Interestingly, the cycloaddition reaction was performed at room temperature under mild conditions and in excellent yields (Scheme 3).…”

Section: Pyrrolesmentioning

confidence: 99%