Highly Stereoselective Synthesis of α-Oxoketene N,X-Acetals (X = O, S, or N) under Mild Conditions DOI
Jiacheng Li, Jiawang Li, Rui Zhang

et al.

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

Published: Feb. 17, 2025

A straightforward synthesis of α-oxoketene N,X-acetals (X = O, S, or N) from β-oxoamides has been described. The oxyphosphonium intermediates are quickly generated in situ the presence Hendrickson reagent and triflic anhydride (Tf2O) a chemoselective manner undergo nucleophilic substitution with phenols, thiophenols, aromatic amines to deliver desired products high stereoselectivity. one-pot synthetic protocol features readily available starting materials, mild conditions, simple execution, wide range potentials products.

Language: Английский

Synthetic and medicinal perspective of quinolines as antiviral agents DOI Open Access
Ramandeep Kaur, Kapil Kumar

European Journal of Medicinal Chemistry, Journal Year: 2021, Volume and Issue: 215, P. 113220 - 113220

Published: Jan. 24, 2021

Language: Английский

Citations

149

Domino C-H Sulfonylation and Pyrazole Annulation for Fully Substituted Pyrazole Synthesis in Water Using Hydrophilic Enaminones DOI
Y. P. Guo, Guodong Wang, Wei Li

et al.

The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 84(5), P. 2984 - 2990

Published: Feb. 4, 2019

The cascade reactions between NH2-functionalized enaminones and sulfonyl hydrazines have been developed for the synthesis of fully substituted pyrazoles. By making use hydrophilic primary amino group in enaminones, proceed well medium pure water presence molecular iodine, TBHP, NaHCO3 via C-H sulfonylation pyrazole annulation. cleavage C–N bond is confirmed by experiment using 15N-labeled enaminone.

Language: Английский

Citations

96

Photo-Thermo-Mechanochemical Approach to Synthesize Quinolines via Addition/Cyclization of Sulfoxonium Ylides with 2-Vinylanilines Catalyzed by Iron(II) Phthalocyanine DOI
Luyao Liu,

Jingyang Lin,

Mingxuan Pang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(5), P. 1146 - 1151

Published: Feb. 3, 2022

A novel photo-thermo-mechanochemical approach to assembling quinolines catalyzed by iron(II) phthalocyanine has been realized for the first time. This transformation features a cost-efficient catalytic system and operational simplicity, is free of solvent, shows good substrate tolerance, providing green alternative existing thermal approaches. Mechanistic experiments demonstrate that in-situ-formed secondary amine may be key intermediate further cyclization/aromatization process.

Language: Английский

Citations

30

Hydroxyl-Directed Rh(III)-Catalyzed C–H Functionalization: Access to Benzo[de]chromenes DOI

Xing-Mei Hu,

Rong Huang,

Qiu‐Lin Wen

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(10), P. 1622 - 1627

Published: March 3, 2023

A cascade oxidative annulation reaction of heterocyclic ketene aminals (HKAs) with internal alkynes catalyzed by [Cp*RhCl2]2 and oxidized Cu(OAc)2·H2O was developed to efficiently synthesize highly functionalized benzo[de]chromene derivatives in good excellent yields. The proceeded the sequential cleavage C(sp2)-H/O-H C(sp2)-H/C(sp2)-H bonds. These multicomponent reactions were regioselective. In addition, all products exhibited intense fluorescence emission solid state, they demonstrated concentration-dependent quenching presence Fe3+, indicating that these compounds could be used recognition Fe3+.

Language: Английский

Citations

23

Recent Advances in the Synthesis of Fused‐Cyclic Quinolines DOI

Shahab A. Darbandizadeh,

Saeed Balalaie

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(5)

Published: Feb. 16, 2024

Abstract Fused quinolines have gained substantial attention due to their significant biological and wide‐spectrum synthetic applications. This review supplies an encyclopedic document regarding the approaches developed for synthesis of fused‐cyclic based on ring volume size reported thus far. collected information will be valuable medicinal chemists obtain knowledge designing new in order access active compounds.

Language: Английский

Citations

6

Copper-Catalyzed Ring-Opening/Reconstruction of Anthranils with Oxo-Compounds: Synthesis of Quinoline Derivatives DOI
Liang‐Hua Zou, Hao Zhu, Shuai Zhu

et al.

The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 84(19), P. 12301 - 12313

Published: Sept. 4, 2019

A copper-catalyzed protocol for the construction of various 2-aryl(alkyl)-3-acylquinolines or 3-arylquinolines using readily available anthranils and 1,3-diketones aldehydes as starting materials is reported herein. Dioxygen sole oxidant hexafluoroisopropanol solvent play an important role in both procedures. This ring-opening/reconstruction strategy involving N–O bond cleavage C–N/C–C formation features high yields broad substrate scope.

Language: Английский

Citations

41

Choline Chloride-Based Deep Eutectic Systems in Sequential Friedländer Reaction and Palladium-Catalyzed sp3 CH Functionalization of Methyl Ketones DOI Creative Commons
Kumaraswamy Naidu Chitrala, Fazlur‐Rahman Nawaz Khan

ACS Omega, Journal Year: 2019, Volume and Issue: 4(5), P. 8046 - 8055

Published: May 2, 2019

A volatile organic solvent-free and choline chloride (ChCl)-based deep eutectic system (DES)-mediated sp3-CH functionalization of acetophenones 1 with benzyl alcohols 2 to the corresponding α, β-saturated ketones 3 is accounted for. The domino dehydrogenation–aldol condensation (hydrogenation borrowing concept) has been successfully attempted palladium-tetrakis(triphenylphosphine) [Pd(PPh3)4] catalyst–xantphos ligand combination. Furthermore, a sequential Friedländer reaction 2-aminobenzophenone 4 palladium-catalyzed α-alkylation quinolinyl methyl ketone in ChCl-based DES have investigated. C–C bond formation through involves wide scope substrates, high atom efficiency, chemoselectivity, environmentally friendly strategy.

Language: Английский

Citations

39

An environmentally benign multi-component reaction: regioselective synthesis of fluorinated 2-aminopyridines using diverse properties of the nitro group DOI

Xuan-Xuan Du,

Quan‐Xing Zi,

Yumeng Wu

et al.

Green Chemistry, Journal Year: 2019, Volume and Issue: 21(6), P. 1505 - 1516

Published: Jan. 1, 2019

A procedure was developed for the synthesis of fluorinated 2-aminopyridines based on reactions 1,1-enediamines, benzaldehydes and 1,3-dicarbonyl compounds.

Language: Английский

Citations

37

Highly Regioselective and Chemoselective [3 + 3] Annulation of Enaminones with ortho-Fluoronitrobenzenenes: Divergent Synthesis of Aposafranones and Their N-Oxides DOI
Xuebing Chen,

Shun-Tao Huang,

Jie Li

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(8), P. 3032 - 3037

Published: April 1, 2021

A base-promoted unprecedented strategy for the regioselective and chemoselective divergent synthesis of highly functionalized aposafranones their N-oxides has been developed from [3 + 3] annulation enaminones with o-fluoronitrobenzenenes. This novel synthetic offers an alternative method construction are meaningful in fields both biology organic synthesis. The established protocol explores scope enaminones, it expands application nitro-based cyclization.

Language: Английский

Citations

32

Multicomponent Cascade Reaction of 3-Formylchromones: Highly Selective Synthesis of Functionalized 9-Azabicyclo[3.3.1]nonane Derivatives DOI

Ying-Gang Duan,

Xing-Mei Hu,

Xin-Ling Cao

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(17), P. 6866 - 6871

Published: Aug. 19, 2021

A novel protocol for the preparation of functionalized 9-azabicyclo[3.3.1]nonane (ABCN) derivatives from 3-formylchromones, enaminones, and heterocyclic ketene aminals (HKAs) through an unprecedented cascade reaction has been developed by simply refluxing mixture substrates 1–3. As a result, series ABCNs were produced very complex reaction. This can be used in synthesis that are suitable combinatorial parallel syntheses ABCN natural-like products one-pot

Language: Английский

Citations

31