One‐Pot Reactions of Ynones with Isothiocyanates for Accessing 2‐Aminothiophenone and Indole‐Fused/Indole‐Substituted Thiophenone Derivatives DOI

Zefeng Jin,

LI Cui-ying,

Guodong Shen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(24), P. 5151 - 5159

Published: Aug. 29, 2024

Abstract A copper or silver‐catalyzed cascade addition/5‐ exo‐dig cyclization/isomerization reaction of isothiocyanate with ynone has been developed. This strategy enables the synthesis a variety ( Z )‐2‐ylidene‐5‐aminothiophen‐3‐one derivatives diverse substitutions in single vessel. The method is featured pot‐economy as well regio‐ and ‐selectivity. Several biologically active molecules could be modified using this strategy. Moreover, relevant indole‐fused indole‐substituted thiophenone were also assembled one pot by merging other bond formation methods. Based on experiments related reports, pathway triggered addition ynone‐derived radical towards C( sp )‐atom was proposed to elucidate probable process transformation.

Language: Английский

A domino reaction from a sensitive azide: the impact of positional isomerism on chemical reactivity featuring ortho azido/nitro substituted derivatives DOI Creative Commons
Vikranth Thaltiri, Jatinder Singh, Richard J. Staples

et al.

Journal of Materials Chemistry A, Journal Year: 2024, Volume and Issue: 12(16), P. 9546 - 9551

Published: Jan. 1, 2024

This study highlights for the first time impact of positional isomerism on chemical reactivity which involves a domino reaction, salt formation, cyclization, and nucleophilic substitution.

Language: Английский

Citations

10

Electrophotocatalytic Tellurosulfonylation of Alkynes for the Synthesis of β-(Telluro)vinyl Sulfones DOI

Zhiheng Zhao,

Huiping Zhang, Hongyan Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6114 - 6119

Published: July 5, 2024

Difunctionalization of alkynes has gained a lot interest in current organic chemistry. Herein, we developed an electrophotocatalytic multicomponent cascade reaction and indoles with sulfinic acid sodium salts using elemental tellurium as the source. Using synergistic anodic oxidation visible-light irradiation, various β-(telluro)vinyl sulfones have been prepared. This strategy features mild conditions, excellent substrate scope, readily available starting materials, great functional group tolerance.

Language: Английский

Citations

4

Dual Cu/Ir Catalyzed Asymmetric Allylation and Pictet‐Spengler Cyclization: Stereodivergent Access to Chiral Indole Fused 9‐Azabicyclo[4.2.1]nonanes DOI Open Access

Xin‐Lian Liu,

Lu Xiao,

Yi Liu

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 24, 2025

Comprehensive Summary Nitrogen‐containing bridged‐heterocycles and indoles are key subunits of many natural products pharmacologically active molecules. We herein present a bimetallic Cu/Ir catalyzed asymmetric allylation ketimine esters ( E )‐4‐indolyl allyl carbonates followed by acid‐promoted Pictet‐Spengler cyclization sequences, enabling stereodivergent synthesis chiral indole fused 9‐azabicyclo[4.2.1]nonanes containing an eight‐membered ring with one tertiary two quaternary stereogenic centers. This one‐pot sequential protocol features step economy, good substrate tolerance, excellent stereoselective control.

Language: Английский

Citations

0

The Aza-Diels-Alder Reaction Between Cyclic Imine and Aza-ortho-quinone Methide Precursor to Access Polycyclic-fused Tetrahydroquinazoline DOI
Xiaoke Zhang, Lu He, Xuan Zhang

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134665 - 134665

Published: April 1, 2025

Language: Английский

Citations

0

TMSOTf-Promoted Cyclization of Indole-2-methyl-α-aminoketones: Access to 4-Aryl-Substituted β-Carbolines DOI
Xinyu Yang, Jin‐Ming Yang, Bin Wu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(5), P. 1105 - 1109

Published: Jan. 30, 2024

An efficient method to construct 4-aryl-substituted β-carbolines from indole-2-methyl-α-aminoketones via a TMSOTf-promoted annulation reaction was reported. High yield along with wide substrate scope and functional group tolerance make this applicable build various highly potential bioactive β-carboline derivatives.

Language: Английский

Citations

3

Copper‐Catalyzed Fluoroamide‐Directed Remote C(sp3)‐H Bond Functionalization Through Intramolecular Hydrogen Atom Transfer DOI
Xin Lv, Yuhao Yang, Liejin Zhou

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(13)

Published: Feb. 15, 2024

Abstract Direct C−H functionalization is an important strategy for the rapid synthesis of valuable organic molecules. Radical‐involved remote C(sp 3 )‐H based on hydrogen atom transfer (HAT) becomes method enabling selective direct transformation bonds at specific distal position(s). In recent years, copper‐catalyzed fluoroamide‐directed bond through intramolecular HAT has served as a robust and elegant assembly variety functionalized (sulfon)amides related derivatives. This review focuses advances in this area. These transformations proceed effectively with high selectivities good functional group compatibility under mild conditions.

Language: Английский

Citations

3

Room‐Temperature Cascade Electrophilic Addition/Cyclization/Oxidation Reactions: Divergent Selective Synthesis of Brominated 2H‐Chromenes, 2H‐Chromen‐2‐ols and 2H‐Chromen‐2‐ones DOI

Guodong Shen,

Zhanjun Li,

Lingyu Zhao

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(40)

Published: May 17, 2024

The room temperature metal-free cascade electrophilic addition/cyclization/oxidation reactions of (3-phenoxyprop-1-yn-1-yl)benzenes to divergently synthesize various brominated benzopyran derivatives (3-bromo-2H-chromenes, 3-bromo-2H-chromen-2-ols and 3-bromo coumarins) by tuning the amount Br

Language: Английский

Citations

2

Diversity-oriented synthesis of indole-fused scaffolds and bis(indolyl)methane from tosyl-protected tryptamine DOI
Liang Wang,

Xiaopei Song,

Fengxia Guo

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(14), P. 2824 - 2834

Published: Jan. 1, 2024

Diversity-oriented synthesis of indole-1,2-fused 1,4-benzodiazepines, tetrahydro-β-carbolines, and 2,2′-bis(indolyl)methanes is presented by control reaction sites.

Language: Английский

Citations

1

Facile synthesis of dihydroisobenzofuran derivatives via a one-pot sequential Passerini-azide/Ag(I)-catalyzed cyclization process DOI

Yan Luo,

Haifeng Yu,

Yang Li-na

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 158, P. 133984 - 133984

Published: April 13, 2024

Language: Английский

Citations

0

Synthesis of Indole‐Fused Pyrazino[1,2‐a]quinazolinones by Copper(I)‐Catalyzed Selective Hydroamination‐Cyclization of Alkynyl‐tethered Quinazolinones DOI
Xiaoqing Liu,

Yanjie Chen,

Pei‐Sen Zou

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 20, 2024

We described a copper(I)-catalyzed atom economic and selective hydroamination-cyclization of alkynyl-tethered quinazolinones to prepare variety indole-fused pyrazino[1,2-a]quinazolinones in good excellent yields ranging from 39 %-99 % under mild reaction conditions. Control experiments revealed that coordination-directed method quinazolinone moiety with copper(I) was important for the alkynes at N1-atom instead N3-atom quinazolinone. The could be easily performed gram scales some prepared donating groups on indole showed distinct fluorescence emission wavelength blue shift acid

Language: Английский

Citations

0