A new method for the synthesis of plurisubstituted pyrroles

Bashiardes, George; Safir, Imad; Barbot, F.; Laduranty, J.

doi:10.1016/j.tetlet.2003.09.099

Cited by 43 publications

(17 citation statements)

References 5 publications

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“…Typical experimental procedure for the cycloaddition of (S)-2-(4-phenylbut-3-yn-2-yloxy)benzaldehyde 4a 51,52 To a solution of O-propargylic salicylaldehyde 4a (0.5 mmol) in dry toluene were added hydrochloride of amino ester 5a (0.75 mmol) and diisopropyl ethyl amine (0.75 mmol). The resulting solution was heated to reflux and the progress of the reaction was monitored by TLC.…”

Section: General Methodsmentioning

confidence: 99%

“…4,[48][49][50] Bashiardes et al synthesized plurisubstituted pyrroles, pyrrolizines and indolizines using intramolecular [3 + 2] cycloaddition reactions wherein the azomethine ylides were generated in the presence of the achiral/racemic O-substituted propargylic moiety. 51,52 In the present study, we report for the first time, the intramolecular cycloaddition reaction of enantiomerically enriched chiral intermediate (S-O-propargylic salicylaldehyde) to achieve the optically enriched pyrrolidines and a pyrrole derivative via a convenient chemoenzymatic approach.…”

Section: Chemoenzymatic Synthesis Of Enantiomerically Enriched Polycy...mentioning

confidence: 96%

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Utilization of whole cell mediated deracemization in a chemoenzymatic synthesis of enantiomerically enriched polycyclic chromeno[4,3-b] pyrrolidines

Saravanan¹,

Jana²,

Chadha³

2014

Org. Biomol. Chem.

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Various aryl and alkyl substituted optically pure propargyl alcohols were obtained with excellent ee (up to >99%) and isolated yields (up to 87%) by deracemization using whole cells of Candida parapsilosis ATCC 7330. The whole cells show substrate specificity towards alkyl substituted propargyl alcohols and a switch in the enantioselectivity has been observed from 'R' to 'S' upon increasing the chain length. For the first time, enantiopure (R)-4-(3-hydroxybut-1-ynyl)benzonitrile, (R)-4-(biphenyl-4-yl)but-3-yn-2-ol, (S)-ethyl 3-hydroxy-5-phenylpent-4-ynoate and (S)-4-phenylbut-3-yne-1,2-diol were obtained using this strategy. Optically pure propargyl alcohol thus obtained was used as a chiral starting material in the synthesis of enantiomerically enriched poly-substituted pyrrolidines and a pyrrole derivative successfully demonstrating a chemoenzymatic route.

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Section: General Methodsmentioning

confidence: 99%

Section: Chemoenzymatic Synthesis Of Enantiomerically Enriched Polycy...mentioning

confidence: 96%

Utilization of whole cell mediated deracemization in a chemoenzymatic synthesis of enantiomerically enriched polycyclic chromeno[4,3-b] pyrrolidines

Saravanan¹,

Jana²,

Chadha³

2014

Org. Biomol. Chem.

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“…Other alternatives include the synthesis and further lactonization of 2‐arylpyrrole derivatives, the Cadogan reaction, oxidative C−H/C−H coupling strategies, and the oxidation of precursors . Some of these methods have limitations such as substrate generality and availability of synthetic precursors, which may restrict their use.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Chromeno[4,3‐b]pyrrol‐4(1H)‐ones, from β‐Nitroalkenes and 4‐Phenylaminocoumarins, under Solvent–free Conditions

et al. 2017

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A new approach toward chromeno[4,3‐b]pyrrol‐4(1H)‐ones, by annulation of 4‐phenylaminocoumarins with β‐nitroalkenes, is reported and its conditions were optimized. The transformations under the fine‐tuned conditions took place under promotion by TsOH.H2O, in the absence of solvent. The scope and limitations of the process were explored, by systematic modification of two diversification points. A reaction mechanism, triggered by a Michael addition of the nitrogen moiety of the 4‐phenylaminocoumarins to the β‐nitroalkene, was also proposed. Further functionalization of a selected tricycle was performed; the photophysical (UV and fluorescence spectra; 1O2 generation) and electrochemical (cyclic voltammetry) properties of some heterocycles were studied.

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“…However, in contrast to well‐developed 1,3‐DCs using olefins as dipolarophiles, 1,3‐DCs of azomethine ylides with alkynes are rather limited, which have sporadically been described in last decades (eq. 2) [2b‐2e,5]. Therefore, this transformation has remained a formidable challenge.…”

Section: Introductionmentioning

confidence: 99%

Brønsted Acid‐Catalyzed Three‐Component 1,3‐Dipolar Cycloadditions of 1,2‐Disubstituted Alkynes with Aldehyde‐Generated Azomethine Ylides

Tan

Guo

et al. 2014

Journal of Heterocyclic Chem

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The first 1,3‐dipolar cycloadditions (1,3‐DCs) of 1,2‐disubstituted alkynes with aldehyde‐generated azomethine ylides have been established, leading to the efficient synthesis of poly‐substituted 2,5‐dihydropyrroles.The Brønsted acid‐catalyzed three‐component 1,3‐DCs of but‐2‐ynedioates, aldehydes, and diethyl 2‐aminomalonate tolerate a wide range of substrates, offering structurally diverse poly‐substituted 2,5‐dihydropyrroles in high yields. This protocol not only provides an easy and efficient approach to poly‐substituted 2,5‐dihydropyrroles but also greatly enriches the chemistry of 1,3‐DCs, especially alkyne‐involved 1,3‐DCs.

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A new method for the synthesis of plurisubstituted pyrroles

Cited by 43 publications

References 5 publications

Utilization of whole cell mediated deracemization in a chemoenzymatic synthesis of enantiomerically enriched polycyclic chromeno[4,3-b] pyrrolidines

Utilization of whole cell mediated deracemization in a chemoenzymatic synthesis of enantiomerically enriched polycyclic chromeno[4,3-b] pyrrolidines

Synthesis of Chromeno[4,3‐b]pyrrol‐4(1H)‐ones, from β‐Nitroalkenes and 4‐Phenylaminocoumarins, under Solvent–free Conditions

Brønsted Acid‐Catalyzed Three‐Component 1,3‐Dipolar Cycloadditions of 1,2‐Disubstituted Alkynes with Aldehyde‐Generated Azomethine Ylides

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