Palladium-catalysed imidoylative spirocyclization of 3-(2-isocyanoethyl)indoles DOI
Shi Tang, Shumin Ding, Dan Li

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(81), P. 10576 - 10579

Published: Jan. 1, 2021

A palladium-catalysed construction of spiroindolines through dearomative spirocyclization 3-(2-isocyanoethyl)indoles has been developed. 2'-Aryl-, vinyl-, and alkyl-substituted could be accessed under mild conditions with excellent functional group tolerance. C1-tethered oxindole- indole-spiroindoline bisheterocycles were generated in high yields via alkene/allene insertion an imidoylative cascade. Additionally, a tandem dearomatization two different indoles was realized N-(2-bromobenzoyl)indoles as the electrophilic coupling partner 3-(2-isocyanoethyl)indoles, affording polyindoline - spiroindoline bisheterocyclic scaffolds conveniently. Under catalysis Pd(OAc)2 spinol-derived phosphoramidite ligand, chiral successfully up to 95% yield 85% ee.

Language: Английский

Advances in palladium-catalysed imidoylative cyclization of functionalized isocyanides for the construction of N-heterocycles DOI
Jian Wang, Dan Li, Jing Li

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(31), P. 6730 - 6745

Published: Jan. 1, 2021

Palladium-catalysed isocyanide insertion reactions have witnessed great progress in recent years.

Language: Английский

Citations

38

Convenient synthesis of spiroindolenines from tryptamine-derived isocyanides and organic azides by cobalt catalysis in pure water DOI
Shuai Jiang, Wenbin Cao, Haiyan Li

et al.

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(7), P. 2619 - 2623

Published: Jan. 1, 2021

A sustainable synthesis of spiroindolenines from tryptamine-derived isocyanides and organic azides in pure water was described.

Language: Английский

Citations

37

Reductive CO2 Fixation via the Selective Formation of C–C Bonds: Bridging Enaminones and Synthesis of 1,4-Dihydropyridines DOI
Yulei Zhao,

Xuqiang Guo,

Xin Ding

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(21), P. 8326 - 8331

Published: Oct. 12, 2020

Herein, a selective tandem C–C bond-forming reaction with CO2 was developed to realize the bridging of enaminones and synthesis 1,4-dihydropyridines, respectively. n-Butylamine significantly promoted this deoxymethylenation procedure catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) ZnCl2. The mechanism involving formation bis(silyl)acetal, nucleophilic addition, amine elimination also interpreted clarify two molecules generation dihydropyridine derivatives.

Language: Английский

Citations

39

Synthesis of polycyclic spiro-fused indolines via IBX-mediated cascade cyclization DOI
Zhiguo Zhang, Xiaoqing Song, Guofeng Li

et al.

Chinese Chemical Letters, Journal Year: 2020, Volume and Issue: 32(4), P. 1423 - 1426

Published: Nov. 2, 2020

Language: Английский

Citations

38

Silver-Catalyzed Cascade Cyclization Reaction of Isocyanides with Sulfoxonium Ylides: Synthesis of 3-Aminofurans and 4-Aminoquinolines DOI

Yong‐Xin Liang,

Ming Yang, Bowen He

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(19), P. 7640 - 7644

Published: Sept. 15, 2020

A silver-catalyzed cascade cyclization reaction of isocyanides with sulfoxonium ylides has been developed for the first time. This provides a new and efficient method construction highly functionalized 3-aminofurans 4-aminoquinolines from readily available starting materials in single step.

Language: Английский

Citations

36

Synthesis of Polysubstituted Benzo[b][1,5]naphthyridine via Mn(III)-Mediated Domino Cascade Reactions of Cyclopropanols and 2-(2-Isocyanophenyl)acetonitriles DOI

Shiqiang Mu,

Qingqing Xuan,

Ying Luo

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

Domino cascade reactions, which can construct multiple bonds in one pot, are efficient methods to synthesize N-heterocycles and other useful skeletons. Herein, we report an expedient synthesis of polysubstituted benzo[b][1,5]naphthyridine via Mn(III)-mediated C–C bond cleavage cyclopropanols. These reactions were initiated by addition β-carbonyl radicals, generated from cyclopropyl alcohols the presence Mn(III), 2-(2-isocyanophenyl)acetonitriles give quinolin-3-amines, went through intramolecular cyclizations dehydrogenation final products.

Language: Английский

Citations

0

Mn(III) Catalyzed Cascade Cross-coupling / Annulation / C(O)-C Bond Insertion / Rearrangement: Access to Multi-substituted Indolenines in Water DOI Creative Commons
Huimin Qian, Shuai Jiang, You Zi

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Language: Английский

Citations

0

Transition-metal-free, three-component trifluoromethylative heteroarylation of unactivated alkenes: Efficient access to β-trifluoromethylated quinoxalinones and preliminary antifungal evaluation against Magnaporthe grisea DOI

Zhuoxian Shao,

Shaoyi Zhang, Yihan Chen

et al.

Tetrahedron, Journal Year: 2020, Volume and Issue: 76(22), P. 131199 - 131199

Published: April 18, 2020

Language: Английский

Citations

32

Catalytic metal-enabled story of isocyanides for use as “C1N1” synthons in cyclization: beyond radical chemistry DOI
Dianpeng Chen, Jianming Li, Xin Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(15), P. 4209 - 4220

Published: Jan. 1, 2022

This review summarizes recent advances in the use of isocyanide as “C1N1” synthons cyclization.

Language: Английский

Citations

17

Fluoroalkylation of Allylic Alcohols with Concomitant (Hetero)aryl Migration: Access to Fluoroalkylated Ketones and Evaluation of Antifungal Action against Magnaporthe grisea DOI
Yanhu Zhang, Ziyang Ren, Yun‐Lin Liu

et al.

European Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 2020(32), P. 5192 - 5200

Published: July 2, 2020

Fluoroalkyl(hetero)arylation of allylic alcohols with perfluoroalkyl iodide or difluoroacetic acid as fluoroalkyl source was developed herein, delivering functionalized ketones containing an α‐quaternary center. Formation the radical followed by its intermolecular addition to alkenes and migration a (hetero)aryl group concomitant generation ketone finish domino sequence. Mechanistic studies indicated that aryl proceeded through neophyl rearrangement in pathway. Moreover, preliminary antifungal evaluation against Magnaporthe grisea is also described for first time.

Language: Английский

Citations

26