Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles DOI Creative Commons
Andrés Arribas, Martín Calvelo, Alejandro Rey

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(36)

Published: June 5, 2024

Abstract Pyrroles and indoles bearing N ‐allenyl tethers participate in a variety of iridium‐catalyzed cycloisomerization processes initiated by C−H activation step, to deliver diversity synthetically relevant azaheterocyclic products. By appropriate selection the ancillary ligand substitution pattern allene, reactions can diverge from simple intramolecular hydrocarbonations tandem involving intriguing mechanistic issues. Accordingly, wide range heterocyclic structures ranging dihydro‐indolizines pyridoindoles tetrahydroindolizines, as well cyclopropane‐fused tetrahydroindolizines be obtained. Moreover, using chiral ligands, these cascade carried out an enantioselective manner. DFT studies provide insights into underlying mechanisms justify observed chemo‐ regio‐ stereoselectivities.

Language: Английский

Comprehensive Review of Dihydro‐2H‐pyrrol‐2‐one Derivatives DOI Open Access

Benjamin Siddiqui,

Chandra Shekhar Yadav,

Mohd Faiyyaz

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(1)

Published: Jan. 1, 2025

Abstract Heterocyclic chemistry has emerged as a significant field with diverse applications in recent scenarios. Nitrogen‐containing heterocyclic compounds have garnered attention due to their unique physiological characteristics and extensive medicinal utility. Therefore, the dihydro‐2 H ‐pyrrol‐2‐one scaffold is key skeleton for pharmaceutical research its high bioavailability wider synthetic applications. This study found that 1,5‐dihydro‐2 scaffolds can be used many ways. Thus, these been subject of lot years, but preparation main core harder because structure. covers methods over past 15 years synthesize substituted derivatives through variety reaction approaches by utilizing hybrid catalyzing systems, including photocatalysis, electrocatalysis, alkaline catalysts, acid organocatalysts, ionic liquid nanocatalysts, heterogeneous or homogeneous transitional‐metal catalysis (including Cu, Pd, Ni, Ru, Co, Fe, Si, Pt, Zn, etc.), well mechanism. review will encourage researchers exploit catalytic synthesis target compounds.

Language: Английский

Citations

0
Solvent-involved synthesis of pyrrolidin-5-one-2-carboxamides via a sequential Ugi/olefination reaction DOI
Na Chen,

Tianyu Long,

Han‐Han Kong

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2780 - 2785

Published: Jan. 1, 2024

An unprecedented multi-component reaction with solvent participation and a novel conversion of sulfur ylides was developed via Ugi/olefination to construct pyrrolidin-5-one-2-carboxamides.

Language: Английский

Citations

0
Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles DOI Creative Commons
Andrés Arribas, Martín Calvelo, Alejandro Rey

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(36)

Published: June 5, 2024

Pyrroles and indoles bearing N-allenyl tethers participate in a variety of iridium-catalyzed cycloisomerization processes initiated by C-H activation step, to deliver diversity synthetically relevant azaheterocyclic products. By appropriate selection the ancillary ligand substitution pattern allene, reactions can diverge from simple intramolecular hydrocarbonations tandem involving intriguing mechanistic issues. Accordingly, wide range heterocyclic structures ranging dihydro-indolizines pyridoindoles tetrahydroindolizines, as well cyclopropane-fused tetrahydroindolizines be obtained. Moreover, using chiral ligands, these cascade carried out an enantioselective manner. DFT studies provide insights into underlying mechanisms justify observed chemo- regio- stereoselectivities.

Language: Английский

Citations

0
Skeletal and Mechanistic Diversity in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles DOI Creative Commons
Andrés Arribas, Martín Calvelo, Alejandro Rey

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(36)

Published: June 5, 2024

Abstract Pyrroles and indoles bearing N ‐allenyl tethers participate in a variety of iridium‐catalyzed cycloisomerization processes initiated by C−H activation step, to deliver diversity synthetically relevant azaheterocyclic products. By appropriate selection the ancillary ligand substitution pattern allene, reactions can diverge from simple intramolecular hydrocarbonations tandem involving intriguing mechanistic issues. Accordingly, wide range heterocyclic structures ranging dihydro‐indolizines pyridoindoles tetrahydroindolizines, as well cyclopropane‐fused tetrahydroindolizines be obtained. Moreover, using chiral ligands, these cascade carried out an enantioselective manner. DFT studies provide insights into underlying mechanisms justify observed chemo‐ regio‐ stereoselectivities.

Language: Английский

Citations

0