Catalytic Intermolecular [4+2]-Cycloaddition toward the Stereo­selective C2–C3 Annulation of Indoles

Soumen Pandit; Nilanjana Majumdar

doi:10.1055/a-2383-7416

Synthesis, Inhaltsverzeichnis

Synthesis 2025; 57(02): 362-379
DOI: 10.1055/a-2383-7416

short review

Special Topic Dedicated to Prof. H. Ila

Catalytic Intermolecular [4+2]-Cycloaddition toward the Stereoselective C2–C3 Annulation of Indoles

Soumen Pandit

^aMedicinal & Process Chemistry Division, CSIR-Central Drug Research Institute (CDRI), Sector 10, Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow 226031, Uttar Pradesh, India

,

Nilanjana Majumdar ∗

^aMedicinal & Process Chemistry Division, CSIR-Central Drug Research Institute (CDRI), Sector 10, Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow 226031, Uttar Pradesh, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India

› Institutsangaben

Abstract

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Abstract

Catalytic dearomative cycloaddition involving the C2–C3 bond of indoles is a powerful strategy for the synthesis of fused indoline scaffolds. Through dearomative 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 have tremendous potential for discovering therapeutic properties, and this strategy has become an important part of the medicinal chemistry toolbox. Using appropriate catalyst control, desirable stereoselectivity can be achieved. Previous literature reports reveal that [3+2]-cycloadditions of indoles have been extensively studied. In contrast, the catalytic [4+2]-cycloaddition/dearomatization of indoles has been much less investigated. In this short review, we focus specifically on six-membered ring annulations via [4+2]-cycloaddition with the C2–C3 bond of indoles and discuss the various catalytic methods that have been developed toward this objective.

1 Introduction

2 [4+2]-Cycloaddition/Annulation of Indoles

2.1 Electron-Rich Indoles

2.1.1 Transition-Metal Catalysis

2.1.2 Organocatalysis

2.2 Electron-Deficient Indoles

2.2.1 Transition-Metal Catalysis

2.2.2 Organocatalysis

3 Summary and Outlook

Key words

cycloaddition - indoles - six-membered-ring annulation - transition-metal catalysis - organocatalysis

Volltext

Referenzen

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Catalytic Intermolecular [4+2]-Cycloaddition toward the Stereo­selective C2–C3 Annulation of Indoles

Catalytic Intermolecular [4+2]-Cycloaddition toward the Stereoselective C2–C3 Annulation of Indoles