Recent Advancements in Pyrrole Synthesis

Synthesis, Journal Year: 2021, Volume and Issue: 53(09), P. 1531 - 1555

Published: March 17, 2021

This review article features selected examples on the synthesis of functionalized pyrroles that were reported between 2014 and 2019. Pyrrole is an important nitrogen-containing aromatic heterocycle can be found in numerous compounds biological material significance. Given its vast importance, pyrrole continues to attractive target for development new synthetic reactions. The contents this are organized by starting materials, which broadly classified into four different types: substrates bearing π-systems, carbonyl other polar groups, heterocyclic motifs. Brief discussions plausible reaction mechanisms most transformations also presented.

Language: Английский

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Lamellarin alkaloids: Isolation, synthesis, and biological activity

˜The œAlkaloids. Chemistry and biology/˜The œalkaloids. Chemistry and biology, Journal Year: 2020, Volume and Issue: unknown, P. 1 - 112

Published: Jan. 1, 2020

Language: Английский

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Weakly Coordinating tert-Amide-Assisted Ru(II)-Catalyzed Synthesis of Azacoumestans via Migratory Insertion of Quinoid Carbene: Application in the Total Synthesis of Isolamellarins

Organic Letters, Journal Year: 2022, Volume and Issue: 24(25), P. 4536 - 4541

Published: June 23, 2022

A weakly coordinating tert-amide-directed straightforward method was developed for the synthesis of azacoumestans using corresponding azaheterocycle derivatives and diazonaphthoquinones under cheap Ru(II)-catalyzed conditions. The reaction proceeds via migratory insertion quinoid carbene subsequent Brønstead acid-mediated cyclization. optimized C2-selective offered a wide scope important azaheterocycles. Bioactive natural products like isolamellarins B were synthesized protocol. Preliminary mechanistic studies highlighted probable pathway.

Language: Английский

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Convergent Total Synthesis of Lamellarins and Their Congeners

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(13), P. 8603 - 8617

Published: May 28, 2020

A convergent total synthesis of lamellarins S and Z is described. The features a halogen dance an easily accessible α,β-dibromopyrrole promoted by ester moiety. resultant β,β′-dibromopyrrole undergoes ligand-controlled Suzuki–Miyaura coupling to provide range diarylated pyrrole derivatives. established synthetic method was also applicable the ningalin B lukianols B.

Language: Английский

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Divergent Conversion of Double Isocyanides with Alkenyl Bromide to Polysubstituted Pyrroles and 4-Imino-4,5-dihydropyrrolo[3,4-b]pyrrol-6(1H)-one Derivatives by Pd-Catalyzed Tandem Cyclization Reactions

Organic Letters, Journal Year: 2022, Volume and Issue: 24(3), P. 859 - 863

Published: Jan. 12, 2022

Herein a novel and concise approach to pyrrole skeletons via Pd-catalyzed tandem cyclization reactions is investigated. The substrates for the transformation could be readily prepared by phosphoric acid-catalyzed Ugi with available starting materials. In this strategy, two isocyanides participate in sequential isocyanide insertion reactions, chemoselectivity of products regulated steric hindrance isocyanide. A plausible mechanism formation corresponding adducts proposed.

Language: Английский

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Recent advances in metal-free catalysts for the synthesis of N-heterocyclic frameworks focusing on 5- and 6-membered rings: a review

RSC Advances, Journal Year: 2025, Volume and Issue: 15(13), P. 9676 - 9755

Published: Jan. 1, 2025

The tremendous potential of transition metal-free multi-component reactions (MCR) in the synthesis N-heterocyclic frameworks is examined this review, offering a complete overview subject matter. discussion on mechanistic rationale reaction routes and intermediates provides profound insights into underlying changes, encouraging deeper investigation various molecular frameworks. This review serves as doorway to study practicality exploiting these for efficient uncomplicated specific nitrogen heterocycles. Specifically, we reveal catalysts field. Because their extensive scope diversity, enable heterocycles that contain nitrogen, which include 5-membered (carbazole, pyrimidines, pyrroles) 6-membered rings (piperidine, pyridine, quinoline, diazinane, pyrazine, quinoxaline, 1,2,3-triazine). In addition, compatibility with functional groups substrates not only increases synthetic value compounds but also broadens relevance domains medical chemistry, materials science, other relevant areas study. To motivate future development field, successful examples described highlight powerful instruments quick general, thorough insightful examination catalysts, highlighting contemporary organic revolutionize field heterocycle synthesis.

Language: Английский

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Thermal vs. Visible‐Light Photoredox‐Catalyzed Cascade Radical Cyclization Involving SO₂ Fixation to Access 6‐Alkylsulfonylmethyl Phenanthridines

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(5)

Published: March 5, 2024

Abstract Convenient access to 6‐alkylsulfonylmethyl phenanthridines has been demonstrated both under non‐catalytic thermal and visible‐light photoredox‐catalyzed conditions. A cascade of radical cyclization is triggered by the exposure biphenyl vinyl azides in‐situ generated alkyl sulfonyl radicals from 4‐substituted Hanztsch esters in presence an SO 2 surrogate. Transition metal‐free, mild reaction conditions, broad substrate scope constitute some highlights approach. Also, synthetic utility accessed demonstrated.

Language: Английский

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Regiodivergent Synthesis of Penta-Substituted Pyrroles through a Cascade [3 + 2] Cyclization of C-Acylimines with Activated Alkynes and Aromatic Nucleophiles

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(10), P. 6697 - 6708

Published: April 22, 2020

Highly robust one-pot, four-component cascade cyclization reaction of α-keto aldehydes, anilines, activated alkynes, and aromatic nucleophiles is developed to synthesize a diverse range pharmaceutically important penta-substituted pyrroles. The proceeds through the acylimines (in situ formed) with alkynes such as indoles, pyrroles, naphthols at room temperature under calcium(II) catalysis high yields broad substrate diversity.

Language: Английский

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Bromonitroalkenes as efficient intermediates in organic synthesis

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(24), P. 4801 - 4838

Published: Jan. 1, 2024

Bromonitroalkenes are useful molecules in synthetic organic chemistry. They mainly prepared from nitroalkenes

Language: Английский

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Concise and Scalable Total Syntheses of Lamellarin Z and other Natural Lamellarins

ChemistrySelect, Journal Year: 2020, Volume and Issue: 5(45), P. 14510 - 14514

Published: Dec. 4, 2020

Abstract An efficient construction of the central 1,2,4‐trisubstituted pyrrole core via one‐pot [3+2] cycloaddition/elimination/aromatization sequence‐based domino process and subsequent Pd‐mediated cross dehydrogenative coupling between C−H bonds peripheral aryl rings enables rapid access to pentacyclic coumarin‐pyrrole‐isoquinoline scaffolds which were smoothly elaborated targeted lamellarins alkaloids. The total synthesis Z S with highest overall yield reported till date, besides several other natural have been realized in 5–6 steps yields ranging from 20–27 %.

Language: Английский

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