Silver-catalyzed tandem cycloisomerization/hydroarylation reactions and mechanistic investigations for an efficient access to 1,2-dihydroisoquinolines

Abreu, Maxime De; Tang, Yue; Brachet, Etienne; Selkti, Mohamed; Michelet, Véronique; Belmont, Philippe

doi:10.1039/d0ob02197k

Cited by 14 publications

(7 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Organic & Biomolecular Chemistry Belmont et al developed a promising silver-catalyzed procedure for the synthesis of 1,2-dihydroisoquinolines 122 via cascade hydroarylation/cycloisomerization processes. 84 The ortho-alkynyl arylaldimines 120 and heterocyclic nucleophiles 121 were simultaneously reacted at room temperature in MeCN for 16 h under the synergistic action of a 5 mol% AgOTf 26 catalyst and 1.1 equiv. acetic acid additive (Scheme 43).…”

Section: Reviewmentioning

confidence: 99%

Silver-catalyzed synthesis of nitrogen heterocycles: recent advancements

2023

View full text Add to dashboard Cite

show abstract

Section: Reviewmentioning

confidence: 99%

Silver-catalyzed synthesis of nitrogen heterocycles: recent advancements

2023

View full text Add to dashboard Cite

show abstract

“…2018 年, 江焕峰和伍婉卿课题组 [73] 报道了一例铜催化芳基腈与邻炔基芳胺合成喹唑啉类化合物的反应 (Scheme 41 2021 年, Belmont 课题组 [77] 发展了一类银催化邻炔基芳亚胺与吲哚串联环化构建 1,2-二氢异喹啉衍生物的反应(Scheme 45). 该反应能够通过引入具有不同生物活性的吲哚骨架来调节二氢异喹啉衍生物的生物活性, 而且产物具有多个官能团修饰位点, 为合成具有生物活性的新型杂环药物提供了一种新方法.…”

Section: 不饱和烃参与的喹啉类化合物的构建unclassified

Recent Advances in the Synthesis of Fused Heterocyclic Compounds and Their Antitumor Activities

Duan¹,

Tang²,

Wu³

2023

Chinese Journal of Organic Chemistry

View full text Add to dashboard Cite

The unique physicochemical properties invest fused heterocyclic compounds with wide applications in the synthesis of natural products, drugs, superconducting materials, energy storage materials, polymer materials, organic dyes, etc. In recent years, the rapid development of transition metal-catalyzed reactions of unsaturated hydrocarbons has developed rapidly. Owing to the advantages of high step-and atom-economy, easy availability of raw starting materials, and efficient construction of carbon-carbon bonds or/and carbon-hetero bonds, it is a vital way to synthesize fused heterocyclic compounds. Herein, the recent progress on the reaction development of transition metal-catalyzed cyclizations involving unsaturated hydrocarbons for the synthesis of fused heterocyclic compounds including benzofurans, indoles, quinolines in the last five years has been summarized, as well as their applications in the field of medicinal chemistry with antitumor activities. Keywords unsaturated hydrocarbons; transition metal-catalysis; fused heterocyclic compounds; antitumor activity 稠杂环化合物是指苯环与杂环或杂环与杂环稠合在一起的化合物(如吲哚、喹啉、嘌呤等 [1][2][3] ). 由于稠杂环化合物通常具有独特的生物活性、低毒性和高内吸收性 [4][5][6][7] , 经常用作医药活性分子和农药的结构单元 [8][9][10][11] . 到目前为止, 全球销售额前 200 的药物中许多化合物含有稠杂环结构(图 1).

show abstract

“…While iodine smoothly promoted the formation of iodo-oxazolone 9, a so far unknown type of derivatives, the corresponding Ag(I)-catalyzed cyclization in (wet) DCE provided the corresponding oxazolone 10 28 via protodesilveration. 57,58 Engaging the pendant aromatic ring in hydroarylation reaction was possible whether by gold(I) catalysis from 8c or by cationic rhodium catalysis 59 from the less activated substrate 8a to provide the corresponding carbazoles 10 and 12.…”

Section: Fig 11 2-iodo-ynamides As Electrophilesmentioning

confidence: 99%

Reactant-Induced Photoactivation of a Gold-Catalyzed Csp2-Csp Cross-Coupling Leading to Indoles

Zhao

Abdellaoui

Berthet

et al. 2021

Preprint

View full text Add to dashboard Cite

A novel access to 2,3-disubstituted indoles from o-alkynyl aniline and iodoalkyne derivatives via a gold-catalyzed sequence under visible-light irradiation and in the absence of an exogenous photocatalyst was uncovered. A wide scope of the process was observed. Of note, 2-iodo-ynamides that have never been used in any organometallic cross-coupling reaction could be used as electrophiles. The resulting N-alkynyl indoles lend themselves to post-functionalization affording valuable scaffolds, notably benzo[a]carbazoles. Mechanistic studies converged on the fact that a potassium sulfonyl amide generates emissive aggregates in the reaction medium. Static quenching of these aggregates by a vinylgold(I) intermediate yields to an excited state of the latter, which can react with an electrophile via oxidative addition and reductive elimination to forge the key C-C bond. This reactant-induced photoactivation of an organogold intermediate opens rich perspectives in the field of cross-coupling reactions.

show abstract

Silver-catalyzed tandem cycloisomerization/hydroarylation reactions and mechanistic investigations for an efficient access to 1,2-dihydroisoquinolines

Abstract: A combination of AcOH and Ag catalyst induced an efficient tandem reaction to form 1,2-dihydroisoquinoline derivatives. Highly functionalized multiheterocyclic scaffolds are accessible straightforwardly using readily available starting materials.

Cited by 14 publications

References 38 publications

Silver-catalyzed synthesis of nitrogen heterocycles: recent advancements

Silver-catalyzed synthesis of nitrogen heterocycles: recent advancements

Recent Advances in the Synthesis of Fused Heterocyclic Compounds and Their Antitumor Activities

Reactant-Induced Photoactivation of a Gold-Catalyzed Csp2-Csp Cross-Coupling Leading to Indoles

Contact Info

Product

Resources

About