PPh3-Mediated cascade reaction of 2-alkynylnitrobenzenes and 1,2-diaminoarenes for the construction of 2-aryl-3-(2-aminoaryl)quinoxalines DOI

Xiaoming Liao,

Yao Xu,

Hui Fan

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 48(2), P. 733 - 737

Published: Dec. 1, 2023

A metal-free strategy to 2-aryl-3-(2-aminoaryl)quinoxalines from 2-alkynylnitrobenzenes and 1,2-diaminobenzenes is developed.

Language: Английский

Organic Synthesis Using Nitroxides DOI
Dirk Leifert, Armido Studer

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(16), P. 10302 - 10380

Published: Aug. 14, 2023

Nitroxides, also known as nitroxyl radicals, are long-lived or stable radicals with the general structure R1R2N–O•. The spin distribution over nitroxide N and O atoms contributes to thermodynamic stability of these radicals. presence bulky N-substituents R1 R2 prevents radical dimerization, ensuring their kinetic stability. Despite reactivity toward various transient C some nitroxides can be easily stored under air at room temperature. Furthermore, oxidized oxoammonium salts (R1R2N═O+) reduced anions (R1R2N–O–), enabling them act valuable oxidants reductants depending on oxidation state. Therefore, they exhibit interesting across all three states. Due fascinating properties, find extensive applications in diverse fields such biochemistry, medicinal chemistry, materials science, organic synthesis. This review focuses versatile For use other important fields, we will refer several articles. introductory part provides a brief overview history chemistry. Subsequently, key methods for preparing discussed, followed by an examination structural diversity physical properties. main portion this is dedicated reactions, wherein parent corresponding serve active species. It demonstrated that functional groups (such alcohols, amines, enolates, alkanes among others) efficiently oxidized. These oxidations carried out using catalysts combination stoichiometric terminal oxidants. By reducing anions, become effective reagents intriguing Nitroxides possess ability selectively react making useful terminating cascade reactions forming alkoxyamines. Depending structure, alkoxyamines weak C–O bonds, allowing thermal generation through reversible bond cleavage. Such thermally generated participate transformations, discussed end review. application strategy natural product synthesis presented.

Language: Английский

Citations

78

Recent advances in electrochemical synthesis of diversely functionalized oxindole derivatives DOI

Xiaocong Zhou,

Ju Wu, Yufen Zhao

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(15), P. 3929 - 3950

Published: Jan. 1, 2023

This review will focus on the electrochemical synthesis of diversified functionalized oxindole derivatives through C-S, C-O, C-C, C-Se, and C-N bond formation over past decade.

Language: Английский

Citations

19

Gold/Chiral Amine Relay Catalysis Enables Asymmetric Synthesis of C2-Quaternary Indolin-3-ones DOI
Wenbin Wang,

Ji-Chao Lu,

Hao Bai

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1792 - 1796

Published: Feb. 28, 2024

A mild and effective strategy for the asymmetric synthesis of C2-quaternary indolin-3-ones from 2-alkynyl arylazides ketones by gold/chiral amine relay catalysis is described. In this reaction, undergo gold-catalyzed cyclization, nucleophilic attack, oxidation to form intermediate 2-phenyl-3H-indol-3-ones, followed an l-proline-catalyzed Mannich reaction with ketones, afford corresponding products in satisfactory yields excellent enantio- diastereoselectivities.

Language: Английский

Citations

5

Electrochemical cascade reactions: an account of recent developments for this modern strategic tool in the arsenal of chemical synthesis DOI
Manoj Kumar Yadav, Sushobhan Chowdhury

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(24), P. 10144 - 10181

Published: Jan. 1, 2023

The electrochemical cascade process majorly satisfies the essential criteria of green synthesis. Being an Integrated synthetic strategy it can produce more molecules in a shorter time and thus provides modern strategic tool arsenal chemists.

Language: Английский

Citations

11

Dearomative ipso-Cyclization to Spiropseudoindoxyls: An Extendable Approach To Access Indolo[3,2-c]quinolinones and Isocryptolepine DOI
Chada Raji Reddy,

Agnuru Theja,

Ejjirotu Srinivasu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 26(1), P. 68 - 72

Published: Dec. 31, 2023

A metal-free oxidative intramolecular dearomative spirocyclization of indole-3-formyl-2-carboxamides has been developed for the first time, affording spiropseudoindoxyls in good yields. This domino process proceeds through sequential oxidation, decarboxylation and ipso-arylation. The unique feature this approach includes compatibility N-protected-indole-2-carboxamides. Further, a hitherto unknown rearrangement to indoloquinolones achieved. synthetic utility strategy also showcased by construction natural alkaloid, isocryptolepine.

Language: Английский

Citations

10

B(C6F5)3-catalyzed regio- and stereoselective cyanation of isatogens and their derivatives DOI

Ryoka Sakai,

Nanaka Ishihara,

Shinji Harada

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 137, P. 154909 - 154909

Published: Jan. 13, 2024

Language: Английский

Citations

3

Recent Developments for the Catalytic Asymmetric Synthesis of Indolin-3-one Derivatives DOI

Atul Jankiram Dolas,

Arun L. Patel,

Imtiyaz Ahmad Shah

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

2,2-Disubstituted indolin-3-ones, which are essential components in many manufactured chemicals, dyes, and naturally occurring bioactive alkaloids, have emerged as exciting synthetic targets. Much attention has been paid to accessing these units, particularly an asymmetric fashion, during the last decade. In this review article, we discuss current state of available methods with existing mechanistic pathways for chiral indolin-3-one derivatives under various catalytic systems. This overall presentation protocols access 2,2-disubstituted or fused indolin-3-ones aza-quaternary centre is categorized based on reaction modes 2-substituted-3H-indole-3-one other similar protocols.

Language: Английский

Citations

0

Synthesis of C2-Spiroindolines Based on the Cascade Reaction of 2-Aryl-3H-indoles with Cyclopropanols DOI

Xueying Yang,

Yuanshuang Xu, Xinying Zhang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 694 - 694

Published: Jan. 1, 2025

Language: Английский

Citations

0

Recent advances in electrocatalytic generation of indole-derived radical cations and their applications in organic synthesis DOI
Wei Zhou, Xi Chen, Lin Lu

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(4), P. 108902 - 108902

Published: Aug. 9, 2023

Language: Английский

Citations

7

2,2-Disubstituted Indoxyls via Oxidative Dearomatization: Generalization to 2-Alkylindoles and Application to Alkaloid Synthesis DOI
Myles W. Smith, Xu Fan

Synlett, Journal Year: 2023, Volume and Issue: 34(13), P. 1539 - 1548

Published: Jan. 26, 2023

Abstract 2,2-Disubstituted indoxyls are commonly found within natural products and bioactive molecules. Among the numerous methods to access such motifs, dearomative transformation of indoles represents an attractive approach. Despite much development, a potential gap exists in oxidative union readily accessible 2-substituted with nucleophilic partners, where general accommodating 2-alkyl substitution broad range nucleophiles is lacking. Herein, we describe development user-friendly solution this challenge highlight its utility synthesis complex alkaloids. 1 Introduction 2 Synthesis Indoxyls via Dearomatization Indoles: Background 3 Oxidative 2-Alkylindoles Indoxyls: Development 4 Selected Scope Preliminary Investigations toward Asymmetric Coupling 5 Application Total Complex Alkaloids 6 Conclusions

Language: Английский

Citations

6