Tandem Michael addition/isocyanide insertion into the C–C bond: a novel access to 2-acylpyrroles and medium-ring fused pyrroles

Zhang, Lingjuan; Xu, Xianxiu; Shao, Qiu-rong; Pan, Ling; Li, Qun

doi:10.1039/c3ob41793j

Cited by 43 publications

(20 citation statements)

References 64 publications

(12 reference statements)

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“…A possible mechanism, for the synthesis of 3,4‐disubstituted pyrroles has been proposed in Scheme . Initially, the Knoevenagel condensation of aldehydes with 1,3‐dicarbonyls in presence of piperidinium acetate results in the formation of intermediate A .…”

Section: Resultsmentioning

confidence: 99%

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Tandem Synthesis of 3,4‐Disubstituted Pyrroles from Aldehydes, 1,3‐Diketones and TosMIC Under Metal‐Free Conditions

et al. 2018

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The method described herein is an efficient and simple process to obtain 3,4‐disubstituted pyrroles. This protocol utilizes the three component reaction of aldehydes, 1,3‐dicarbonyls and TosMIC in one pot under metal free conditions with moderate to excellent yields. The mechanism of the reaction involves a Knoevenagel condensation between an aldehyde and dicarbonyl substrate to give unsaturated alkene intermediate which further undergoes Michael addition with TosMIC to provide desired 3,4‐disubstituted pyrroles. The scope of the substrate was then explored to understand the diversity of functional group tolerance. A series of 31 examples were generated using the present protocol.

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Section: Resultsmentioning

confidence: 99%

“…Recently Liu and Xu et al., developed a copper catalysed synthesis of 2‐acyl pyrroles from TosMIC and acceptor alkenes (Figure ), where metal assisted acyl migration was observed. In another report, 3,4‐disubstituted pyrroles were obtained from Indanones, aldehydes and TosMIC under copper catalysis .…”

Section: Introductionmentioning

confidence: 99%

Tandem Synthesis of 3,4‐Disubstituted Pyrroles from Aldehydes, 1,3‐Diketones and TosMIC Under Metal‐Free Conditions

et al. 2018

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“…Both the products were separated using column chromatography and very well characterized using spectroscopic techniques. [15]…”

Section: Synthesis Of Pyrrole Scaffoldmentioning

confidence: 99%

TosMIC: A Powerful Synthon for Cyclization and Sulfonylation

Kumar

2020

ChemistrySelect

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p‐tosylmethyl isocyanide (TosMIC) which is also known as van Leusen's reagent hold the three functionalized groups including the isocyanide and sulfonyl group and an alpha carbon which is acidic by nature. Tosyl set of this fortunate reagent acts as a good leaving group and assist the alpha carbon to contribute in a range of cyclization strategies. Exceptionally, TosMIC was also proved as a good sulfonylating and sulfomethylating reagent. TosMIC has proved as a powerful and versatile synthon and betrothed in the synthesis of broad range of heterocycles having pharmacological interest. This review is focused on synthetic utility of TosMIC in diverse range of heterocycles like five membered heterocycles, fused heterocycles, linked or tethered heterocycles, spiro compounds etc. It is also utilized for regio, chemo and stereoselective synthesis and production of sulfones and sulfinates. It serves as an important building block in various synthetic methodologies like multi component reaction, cyclization, domino, cascade and cycloaddition and metal catalysed reactions. Various new catalyst and novel methodologies were explored due to enormous use of this wonderful reagent.

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“…(130)]. [180] Catalytic copper chloride and stoichiometric DBU provide the optimal combination, although CuBr and CuI also catalyze the reaction. Enones bearing electron-withdrawing substituents on the a-carbon are suitable substrates.…”

Section: Miscellaneous Isonitrile Condensationsmentioning

confidence: 99%

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

et al. 2014

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Isonitriles are delicately poised chemical entities capable of being coaxed to react as nucleophiles or electrophiles. Directing this tunable reactivity with metal and non-metal catalysts provides rapid access to a large array of complex nitrogenous structures ideally functionalized for medicinal applications. Isonitrile insertion into transition metal complexes has featured in numerous synthetic and mechanistic studies, leading to rapid deployment of isonitriles in numerous catalytic processes, including multicomponent reactions (MCR). Covering the literature from 1990–2014, the present review collates reaction types to highlight reactivity trends and allow catalyst comparison.

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Tandem Michael addition/isocyanide insertion into the C–C bond: a novel access to 2-acylpyrroles and medium-ring fused pyrroles

Abstract: A new reaction model, tandem Michael addition/formal isocyanide insertion into the acyl C-C bond, has been developed. Thus, a series of 2-acylpyrroles and seven-/eight-membered ring fused pyrroles were synthesized from the reaction of methyl isocyanides with enones in a single operation.

Cited by 43 publications

References 64 publications

Tandem Synthesis of 3,4‐Disubstituted Pyrroles from Aldehydes, 1,3‐Diketones and TosMIC Under Metal‐Free Conditions

Tandem Synthesis of 3,4‐Disubstituted Pyrroles from Aldehydes, 1,3‐Diketones and TosMIC Under Metal‐Free Conditions

TosMIC: A Powerful Synthon for Cyclization and Sulfonylation

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

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