K2S2O8-Mediated Synthesis of Highly Functionalized Pyrroles via Oxidative Self-Dimerization of N-Propargylamines

Behera, Bipin Kumar; Sahu, Archana; Devi, Ngangbam Renubala; Saikia, Anil K.

doi:10.1021/acs.joc.1c00471

Cited by 21 publications

(5 citation statements)

References 68 publications

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“…Deprotonation of the intermediate B occurs to afford the radical tetrahydrocarbazole intermediate C . At the same time, oxidation of sulfinate 2f by K 2 S 2 O 8 generates sulfonyl radical C , which couples with the intermediate C to afford the desired tetrahydrocarbazole product 3af . It should be mentioned that the pathway via the sequence of the intermediate A cationic coupling with alkynyl unit and then direct coupling with sulfonyl anion could not be ruled out.…”

Section: Resultsmentioning

confidence: 99%

Electrochemical Annulation of Indole-Tethered Alkynes Enabling Synthesis of Exocyclic Alkenyl Tetrahydrocarbazoles

Liu

et al. 2023

J. Org. Chem.

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An electrochemical sulfonylation-triggered cyclization reaction of indole-tethered terminal alkynes with sulfinates as sulfonyl sources has been developed, which affords exocyclic alkenyl tetrahydrocarbazoles in good chemical yields. This reaction features convenient operation and tolerates a wide scope of substrates with a variety of electronically and sterically diverse substituents. Furthermore, high E-stereoselectivity is observed for this reaction, which provides an efficient method for the preparation of functionalized tetrahydrocarbazole derivatives.

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Section: Resultsmentioning

confidence: 99%

Electrochemical Annulation of Indole-Tethered Alkynes Enabling Synthesis of Exocyclic Alkenyl Tetrahydrocarbazoles

Liu

et al. 2023

J. Org. Chem.

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“…Regarding the synthesis of pyrroles, there are various synthetic procedures that can be used including the classical Paal–Knorr and Hantzsch reactions [ 30 , 31 , 32 ]. An interesting method of obtaining pyrroles is via the reaction of benzimidazolium salts with dipolarophile alkyne derivatives [ 33 , 34 ].…”

Section: Introductionmentioning

confidence: 99%

New Pyrrole Derivatives as Promising Biological Agents: Design, Synthesis, Characterization, In Silico, and Cytotoxicity Evaluation

Ivan

Bărbuceanu

Hotnog

et al. 2022

IJMS

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The current study describes the synthesis, physicochemical characterization and cytotoxicity evaluation of a new series of pyrrole derivatives in order to identify new bioactive molecules. The new pyrroles were obtained by reaction of benzimidazolium bromide derivatives with asymmetrical acetylenes in 1,2-epoxybutane under reflux through the Huisgen [3 + 2] cycloaddition of several ylide intermediates to the corresponding dipolarophiles. The intermediates salts were obtained from corresponding benzimidazole with bromoacetonitrile. The structures of the newly synthesized compounds were confirmed by elemental analysis, spectral techniques (i.e., IR, 1H-NMR and 13C-NMR) and single-crystal X-ray analysis. The cytotoxicity of the synthesized compounds was evaluated on plant cells (i.e., Triticum aestivum L.) and animal cells using aquatic crustaceans (i.e., Artemia franciscana Kellogg and Daphnia magna Straus). The potential antitumor activity of several of the pyrrole derivatives was studied by performing in vitro cytotoxicity assays on human adenocarcinoma-derived cell lines (i.e., LoVo (colon), MCF-7 (breast), and SK-OV-3 (ovary)) and normal human umbilical vein endothelial cells (HUVECs). The obtained results of the cytotoxicity assessment indicated that the tested compounds had nontoxic activity on Triticum aestivum L., while on Artemia franciscana Kellogg nauplii, only compounds 2c and 4c had moderate toxicity. On Daphnia magna, 4b and 4c showed high toxicity; 2a, 2b, and 2c moderate to high toxicity; only 4a and 4d were nontoxic. The compound-mediated cytotoxicity assays showed that several pyrrole compounds demonstrated dose- and time-dependent cytotoxic activity against all tested tumor cell lines, the highest antitumor properties being achieved by 4a and its homologue 4d, especially against LoVo colon cells.

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“…For example, Kaixiu Luo [12] developed the insert approach to the coupling of enaminones with donor/acceptor or donor/donor carbenes by the AgOTf-catalyzed CÀ C bond carbenoid insertion/ cyclization/ [1,5]-shift cascade reaction for distinct chemo-and regioselective multisubstituted pyrroles. Anil K. Saikia and co-workers [13] reported a radical initiated direct transformation of N-propargylamines into 1,2,3,4,5-pentasubstituted pyrroles having two carbonyl groups in the side chain catalyzed by AgOBz in the presence of K 2 S 2 O 8 . Recently, Wan and co-workers reported the synthesis of NH-free pyrroles by the Pd catalyzed annulation of enaminones and alkenes.…”

Section: Introductionmentioning

confidence: 99%

Green Catalytic Synthesis of the Pyrroles by N and P Functionalized Activated Carbon supported Ir

Sun

Jiang

et al. 2022

ChemistrySelect

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Pyrroles are a significant class of nitrogen-containing heterocyclic compounds and the derivatives. Here, an efficient procedure has been proposed for the loading of Ir on N, Pdoped activated carbon to exploit pyrroles are synthesized from alcohols and amino alcohols. And the optimal conversion of 1-phenylethanol is up to 65 % with 2-phenylpyrrole selectivity of 80 %. The good performance is attributed to the interaction between metal Ir and N, P-doped activated carbon, which could also be confirmed from BET and XPS characterizations. What's more, the catalyst could be generally used for a range of reactions to produce pyrroles from alcohols and amino alcohols.

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K₂S₂O₈-Mediated Synthesis of Highly Functionalized Pyrroles via Oxidative Self-Dimerization of N-Propargylamines

Cited by 21 publications

References 68 publications

Electrochemical Annulation of Indole-Tethered Alkynes Enabling Synthesis of Exocyclic Alkenyl Tetrahydrocarbazoles

Electrochemical Annulation of Indole-Tethered Alkynes Enabling Synthesis of Exocyclic Alkenyl Tetrahydrocarbazoles

New Pyrrole Derivatives as Promising Biological Agents: Design, Synthesis, Characterization, In Silico, and Cytotoxicity Evaluation

Green Catalytic Synthesis of the Pyrroles by N and P Functionalized Activated Carbon supported Ir

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