How electrophilic are 3-nitroindoles? Mechanistic investigations and application to a reagentless (4+2) cycloaddition-Reference-Cited by-同舟云学术

How electrophilic are 3-nitroindoles? Mechanistic investigations and application to a reagentless (4+2) cycloaddition

Published:2021 Issue:78 Volume:57 Page:10071-10074
ISSN:1359-7345
Container-title:Chemical Communications
language:en
Short-container-title:Chem. Commun.

Author:

Rkein Batoul¹,Manneveau Maxime¹,Noël-Duchesneau Ludovik²,Pasturaud Karine¹,Durandetti Muriel¹^ORCID,Legros Julien¹^ORCID,Lakhdar Sami²³^ORCID,Chataigner Isabelle¹⁴^ORCID

Affiliation:

1. Normandie Univ., UNIROUEN, CNRS, INSA Rouen, COBRA, 76000 Rouen, France

2. Normandie Univ., ENSICAEN, Unicaen, CNRS, LCMT, 14000 Caen, France

3. Université Paul Sabatier, Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA, UMR 5069), 118 Route de Narbonne, 31062, Toulouse Cedex 09, France

4. Sorbonne Université, CNRS, Laboratoire de Chimie Théorique, LCT UMR7616, 75005 Paris, France

Abstract

The electrophilicity of 4 different 3-nitroindole derivatives has been evaluated by Mayr's linear free energy relationship (log k(20 °C) = sN(E + N)) and reveals unexpected values for aromatic compounds, in the nitrostyrene range.

Funder

Agence Nationale de la Recherche

European Regional Development Fund

Université de Rouen

Centre National de la Recherche Scientifique

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2021/CC/D1CC04074J

Reference31 articles.

1. Indoles — A promising scaffold for drug development

2. Nucleophilic Reactivities of Indoles

3. W. A.Remers in Chemistry of Heterocyclic Compounds , ed. W. J. Houlihan , John Wiley & Sons, Inc. , 1971 , pp. 1–226

Cited by 11 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Controlling Diastereoselectivity in Dearomatizing Diels‐Alder Reactions of Nitroarenes with 2‐Trimethylsilyloxycyclohexadiene;Chemistry – A European Journal;2024-05-23

2. Tandem Reactions of Electrophilic Indoles toward Indolizines and Their Subsequent Transformations through Pd(II)-Mediated C–H Functionalization to Access Polyring-Fused N-Heterocycles;ACS Omega;2024-03-30

3. Dearomative [4 + 2] cycloaddition of 3‐nitroindoles with ortho‐amino Morita−Baylis−Hillman carbonates to forge indole‐fused quinolines;Journal of Heterocyclic Chemistry;2024-01-16

4. Dichotomic Dearomatizations of Benzene vs Pyridine Rings of Sulfonyloxypyridine via (3 + 2) Cycloaddition;The Journal of Organic Chemistry;2023-08-10

5. Predictive TDDFT Methodology for Aromatic Molecules UV‐Vis properties: from Benchmark to Applications;ChemistrySelect;2023-08