Catalytic Intermolecular [4+2]-Cycloaddition toward Stereoselective C2-C3 Annulation of Indoles DOI
Nilanjana Majumdar,

Soumen Pandit

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 9, 2024

Abstract Catalytic dearomative cycloaddition involving the C2–C3 bond of indoles is a powerful strategy for synthesis fused indoline scaffolds. Through cycloaddition/annulation, planar indole substrates can be readily transformed into rigid, three-dimensional polycyclic complex structures in one step. Molecules with architectural complexity are generally considered to have drug-like properties. Hence, annulation products tremendous potential discovering therapeutic properties, and this has become an important part medicinal chemistry toolbox. Using appropriate catalyst control, desirable stereoselectivity achieved. Previous literature reports reveal that [3+2]-cycloadditions been extensively studied. In contrast, catalytic [4+2]-cycloaddition/dearomatization much less investigated. short review, we focus specifically on six-membered ring annulations via [4+2]-cycloaddition discuss various methods developed toward objective. 1 Introduction 2 [4+2]-Cycloaddition/Annulation Indoles 2.1 Electron-Rich 2.1.1 Transition-Metal Catalysis 2.1.2 Organocatalysis 2.2 Electron-Deficient 2.2.1 2.2.2 3 Summary Outlook

Language: Английский

Dearomative Alkylation-Based Two-Step cis-Diastereoselective Synthesis of Indoline-2,3-Fused Chromans and Tetrahydropyrans DOI

Raju Chouhan,

Nandini Ray,

Nitish Nayan Gogoi

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 3, 2024

Herein, we describe a two-step,

Language: Английский

Citations

4
N-Iodosuccinimide-Promoted Synthesis of Indolo[3,2-c]quinolizines via Cascade Intramolecular C–N Bond Formation/Aromatization with 3-(1H-Indol-3-yl)-2-(pyridin-2-yl)propanoates DOI
Chen Chen, Xixiang Yang, Jiaxin Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 10, 2025

An NIS-promoted cascade of intramolecular C-N bond formation/aromatization with 3-(1H-indol-3-yl)-2-(pyridin-2-yl)propanoates is described for synthesizing a polycyclic indole skeleton, indolo[3,2-c]quinolizine, as well 1,9-dihydropyrazolo[4',3':5,6]pyrido[2,3-b]indole. The advantages this protocol include accessible starting materials, mild conditions, simple operation, and good yields. Indolo[3,2-c]quinolizines exhibited fluorescence properties effective staining live cells, targeting lysosomes mitochondria. Additionally, the products showed significant antiproliferative activity against tumor cells in MTT assay.

Language: Английский

Citations

0
Brønsted Acid‐Assisted Lewis Acid Mediated Intramolecular Trapping of Aminoenol with Activated Alkenes and Ketones DOI

Minakshi Altia,

Pazhamalai Anbarasan

Chemistry - An Asian Journal, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Abstract An efficient Brønsted acid‐assisted Lewis acid‐mediated synthesis of indolines and pyrrolidines has been achieved from α‐hydroxydimethylacetals suitable electrophile‐tethered amines. The reaction proceeds via an interrupted Amadori/Heyns rearrangement, where the key aminoenol intermediate was successfully trapped with Michael acceptors ketones in intramolecular fashion to afford corresponding derivatives good yield diastereoselectivity. is operationally simple, general, tolerates various functional groups.

Language: Английский

Citations

0
Tandem SNAr/Aldol Condensation of Oxindoles with o-Haloacetophenones Enables Modular Assembly of 2,3-Fused Indolines Bearing a Quaternary Carbon DOI
Zhiping Zheng,

Kai-Heng Yu,

Ziyuan Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 28, 2025

Described herein is a novel base-promoted [4 + 2] annulation reaction of 3-methyl-indolin-2-ones with ortho-haloacetophenones, which enables the modular and reliable synthesis 2,3-fused indolines bearing quaternary carbon. Two C-C bonds can be successively constructed through tandem sequence involving SNAr aldol condensation. This protocol highlighted by transition metal-free conditions, high efficiency, simple operation.

Language: Английский

Citations

0
Chiral Brønsted Acid‐Catalyzed Asymmetric Reaction via Vinylidene Ortho‐Quinone Methides DOI
Xin‐Qi Zhu,

Hai‐Yu Yang,

Long‐Wu Ye

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(49)

Published: June 26, 2024

Vinylidene ortho-quinone methides (VQMs) have been proven to be versatile and crucial intermediates in the catalytic asymmetric reaction last decade, thus drawn considerable concentrations on account of practical application construction enantiomerically pure functional organic molecules. However, comparison well established chiral Brønsted base-catalyzed via VQMs, acid-catalyzed is rarely studied there no systematic summary date. In this review, we summarize recent advances VQMs according three types reactions: a) intermolecular nucleophilic addition VQMs; b) cycloaddition c) intramolecular cyclization VQMs. Finally, put forward remained challenges opportunities for potential breakthroughs area.

Language: Английский

Citations

0
Catalytic Intermolecular [4+2]-Cycloaddition toward Stereoselective C2-C3 Annulation of Indoles DOI
Nilanjana Majumdar,

Soumen Pandit

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 9, 2024

Abstract Catalytic dearomative cycloaddition involving the C2–C3 bond of indoles is a powerful strategy for synthesis fused indoline scaffolds. Through cycloaddition/annulation, planar indole substrates can be readily transformed into rigid, three-dimensional polycyclic complex structures in one step. Molecules with architectural complexity are generally considered to have drug-like properties. Hence, annulation products tremendous potential discovering therapeutic properties, and this has become an important part medicinal chemistry toolbox. Using appropriate catalyst control, desirable stereoselectivity achieved. Previous literature reports reveal that [3+2]-cycloadditions been extensively studied. In contrast, catalytic [4+2]-cycloaddition/dearomatization much less investigated. short review, we focus specifically on six-membered ring annulations via [4+2]-cycloaddition discuss various methods developed toward objective. 1 Introduction 2 [4+2]-Cycloaddition/Annulation Indoles 2.1 Electron-Rich 2.1.1 Transition-Metal Catalysis 2.1.2 Organocatalysis 2.2 Electron-Deficient 2.2.1 2.2.2 3 Summary Outlook

Language: Английский

Citations

0