☆ 4.8 Article

Metal-Free Photoinduced Hydrocyclization of Unactivated Alkenes toward Ring-Fused Quinazolin-4(3H)-ones via Intermolecular Hydrogen Atom Transfer

ORGANIC LETTERS (2023)

Related references

Note: Only part of the references are listed.

Article Chemistry, Applied

Photo-Triggered Self-Induced Homolytic Dechlorinative Sulfonylation/Cyclization of Unactivated Alkenes: Synthesis of Quinazolinones Containing a Sulfonyl Group

Bin Sun et al.

Summary: A self-photocatalyzed sulfonylation/cyclization method for quinazolinones with unactivated alkenes and various sulfonyl chlorides has been developed, allowing access to sulfonyl radicals without the need for external photocatalysts or oxidants. This provides an alternative route for synthesizing sulfonylated compounds.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Add to Collection

Article Chemistry, Applied

Radical Polychloromethylation/Cyclization of Unactivated Alkenes: Access to Polychloromethyl-Substituted Ring-Fused Quinazolinones

Han Liu et al.

Summary: A metal-free radical di- and trichloromethylation/cyclization of unactivated alkenes was developed using commercially available dichloromethane and chloroform as di- and trichloromethyl sources. Various di- and trichloromethylated pyrrolo- and piperidino-quinazolinones were obtained in good yields. The dichloromethylated product can be further transformed into a spiro[cyclopropane-1,3'-pyrrolo[2,1-b]quinazolin]-9'(2'H)-one using KOH.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Add to Collection

Article Chemistry, Organic

A Photosensitizer-Free Radical Cascade for Synthesizing CF3-Containing Polycyclic Quinazolinones with Visible Light

Qiang Hu et al.

Summary: Herein, we report an efficient photoinduced radical tandem trifluoromethylation/cyclization reaction for the synthesis of functionalized quinazolinones. The reaction can be carried out under mild conditions without any additional photosensitizer, metal, or extra additives. A series of trifluoromethyl quinazolinones were efficiently prepared with good yields and excellent functional group tolerance, indicating the potential of this method for diverse applications.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Cyanomethylative cyclization of unactivated alkenes with nitriles for the synthesis of cyano-containing ring-fused quinazolin-4(3H)-ones

Han Liu et al.

Summary: A metal-free synthesis method for cyano-containing ring-fused quinazolin-4(3H)-one derivatives was developed, achieving moderate to excellent yields. Additionally, a derivative of the natural product leucomidine C was conveniently synthesized using this method.

NEW JOURNAL OF CHEMISTRY (2022)

Add to Collection

Article Chemistry, Applied

Electrosynthesis of CF3-Substituted Polycyclic Quinazolinones via Cascade Trifluoromethylation/Cyclization of Unactivated Alkene

Lei Liu et al.

Summary: An atom and step economy cascade trifluoromethylation/cyclization of unactivated alkene with Langlois reagent as a CF3 source is successfully demonstrated. The synthesis of a variety of polycyclic quinazolinones was achieved in 52-81% yields without the requirement of transition metal catalysts or oxidants. The use of Langlois reagent in this strategy provides the advantages of bench-stability, cost-effectiveness, and high efficiency. The gram-scale reaction, broad substrate scope, and good functional group tolerance further confirm the synthetic usefulness of this protocol.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Add to Collection

Article Chemistry, Organic

Synthesis of Polycyclic Quinazolinones through C(sp3)-H Functionalization of Inert Alkanes or Visible-Light-Promoted Oxidation Decarboxylation of N-Hydroxyphthalimide Esters

Wei-Kang Zhang et al.

Summary: Two novel methods for the functionalization of inert alkanes and the synthesis of polycyclic quinazolinones through visible-light promoted oxidation decarboxylation have been described. These methods do not require metal catalysts and can be performed in water or water/DMSO media. The wide substrate scope and mild reaction conditions demonstrate the practicality of these strategies.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

Add to Collection

Article Chemistry, Organic

Access to Phosphine-Containing Quinazolinones Enabled by Photo-Induced Radical Phosphorylation/Cyclization of Unactivated Alkenes

Binsong Mu et al.

Summary: A new synthetic method was reported for the efficient synthesis of phosphine-containing quinazolinones, with broad applicability and high atomic economy.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Add to Collection

Article Chemistry, Organic

Organic photoredox catalytic radical sulfonamidation/cyclization of unactivated alkenes towards polycyclic quinazolinones

Changduo Pan et al.

Summary: The synthesis of sulfonamidylated polycyclic quinazolinones was achieved via visible-light-induced cascade N-centered radical addition/cyclization. The easily accessible N-sulfonylaminopyridinium salts were used as the radical source, resulting in high yields (up to 91%) of various sulfonamidylated compounds. This method offers the advantages of operational simplicity, broad substrate scope, and mild reaction conditions.

ORGANIC CHEMISTRY FRONTIERS (2022)

Add to Collection

Review Chemistry, Organic

C-centered radical-initiated cyclization by directed C(sp3)-H oxidative functionalization

Jiao-Zhe Li et al.

Summary: The development of C(sp(3))-H functionalization is challenging and attracting attention. The C-centered radical strategy is a powerful toolbox for constructing valuable molecules, avoiding the limitations of traditional methods. The selection of an oxidation system provides freedom for substrate application and condition optimization. This paper focuses on C-centered radical-initiated cyclization strategies by directed C(sp(3))-H oxidative functionalization.

ORGANIC CHEMISTRY FRONTIERS (2022)

Add to Collection

Review Chemistry, Organic

The synthesis of seven- and eight-membered rings by radical strategies

Xuan-Chi Yu et al.

Summary: Seven- and eight-membered rings are commonly found in natural products and drugs. Their synthesis is challenging due to transition state nonbonding interactions, torsional strains, flexible conformations, and complex multi-ring skeletons. The radical strategy, using metal-induced, oxidant-initiated, electrochemically promoted, or photoinduced systems, offers a powerful tool to overcome the limitations of poor selectivity and harsh reaction conditions. This review highlights recent advances in the synthesis of seven- and eight-membered rings and provides insights into exploring new reaction models in radical chemistry.

ORGANIC CHEMISTRY FRONTIERS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Visible-Light Photosynthesis of CHF2/CClF2/CBrF2-Substituted Ring-fused Quinazolinones in Dimethyl Carbonate

Qing-Wen Gui et al.

Summary: In this study, eco-friendly dimethyl carbonate was utilized as the sole solvent for the visible-light-induced cascade radical reactions, providing an efficient method for constructing CHF2/CClF2/CBrF2-substituted ring-fused quinazolinones.

CHEMISTRY-AN ASIAN JOURNAL (2021)

Add to Collection

Article Chemistry, Organic

Self-Catalyzed Phototandem Perfluoroalkylation/Cyclization of Unactivated Alkenes: Synthesis of Perfluoroalkyl-Substituted Quinazolinones

Bin Sun et al.

Summary: A novel visible-light-induced radical tandem tri-fluoromethylation/cyclization reaction of unactivated alkenes with sodium perfluoroalkanesulfinates has been developed, leading to perfluoroalkyl-substituted quinazoline alkaloids. Remarkably, this transformation can be carried out without the use of any metal catalyst, strong oxidant, or external photosensitizer.

ORGANIC LETTERS (2021)

Add to Collection

Article Chemistry, Organic

Visible-Light-Induced Radical Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Quinazolinones

Xiaoyu Chen et al.

Summary: A mild and efficient visible-light-induced radical difluoromethylation/cyclization of unactivated alkenes toward the synthesis of substituted quinazolinones with easily accessible difluoromethyltriphenylphosphonium bromide has been developed. The transformation has the advantages of wide functional group compatibility, a broad substrate scope, and operational simplicity, providing a facile access to pharmaceutically valuable difluoromethylated polycyclic quinazolinones.

ORGANIC LETTERS (2021)

Add to Collection

Review Chemistry, Multidisciplinary

Catalytic Generation of Carbanions through Carbonyl Umpolung

Shun Wang et al.

Summary: The article summarizes recent progress in the generation of alkyl carbanions through catalytic carbonyl Umpolung, discussing two different catalytic approaches and their reaction scope, mechanistic insights, synthetic applications, and potential future developments.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Review Chemistry, Applied

Radical Cascade Reactions of β,γ-Unsaturated Hydrazones/Oximes

Ya-Feng Si et al.

Summary: This review summarizes and classifies three catalytic ways of radical cascade cyclization of beta,gamma-unsaturated hydrazones/oximes: transition-metal-catalyzed systems, transition-metal-free systems, and photo-/electrocatalytic systems. Through these methods, various functional groups are installed on the pyrazoline and isoxazoline skeletons to enrich the small organic molecule library.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Add to Collection

Article Chemistry, Organic

Metal-Free Hydroxyalkylative Radical Addition/Cyclization of Unactivated Alkenes for the Synthesis of Hydroxyalkylated Ring-Fused Quinazolinones

Zixian Yang et al.

Summary: An efficient protocol for the synthesis of ring-fused quinazolinone derivatives through hydroxyalkyl radical-initiated cyclization was established, providing a series of hydroxyl-containing quinazolinones in moderate to good yields. This metal-free reaction represents the first successful construction of ring-fused quinazolinones through radical C(sp(3))-H functionalization of simple alcohols and was applied in the synthesis of a Phaitanthrin A derivative.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives

Bin Sun et al.

Summary: A novel and green strategy for the synthesis of acylated quinazolinone derivatives has been developed, using a photo-induced decarboxylative cascade radical acylation/cyclization reaction. The reaction proceeds smoothly without the need for external photocatalysts, additives, or oxidants, and can be easily scaled-up under flow conditions with sunlight irradiation.

CHEMICAL COMMUNICATIONS (2021)

Add to Collection

Review Chemistry, Organic

Nitriles as radical acceptors in radical cascade reactions

Kai Sun et al.

Summary: The cyano group as a radical acceptor in cascade reactions offers diverse opportunities for the convenient construction of various important heterocycles and carbocycles, leading to the rapid buildup of molecular complexity. This review focuses on summarizing the dynamic field of radical cascade processes using the cyano group as a radical acceptor, which has not been well documented so far.

ORGANIC CHEMISTRY FRONTIERS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Photo-triggered self-catalyzed fluoroalkylation/cyclization of unactivated alkenes: synthesis of quinazolinones containing the CF2R group

Jin Yang et al.

Summary: A novel photo-triggered self-catalyzed fluoroalkylation/cyclization of quinazolinones containing unactivated alkenes with various fluoroalkyl bromides has been developed. This transformation exhibits excellent substrate generality with respect to both the coupling partners. The method is the first example describing the C-sp(3)-Br bond homolysis of alkyl bromides via a substrate induced energy transfer process, and the mild conditions, tolerance to a wide range of functional groups, and operational simplicity make it practical for the synthesis of fluorine-containing ring-fused quinazolinones.

GREEN CHEMISTRY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Hydrogen Atom Transfer-Mediated Domino Cyclisation Reaction to Access (Spiro)Quinazolinones

Oliver J. Turner et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Add to Collection

Article Chemistry, Medicinal

Recognition of Natural Products as Potential Inhibitors of COVID-19 Main Protease (Mpro): In-Silico Evidences

Rohan R. Narkhede et al.

NATURAL PRODUCTS AND BIOPROSPECTING (2020)

Add to Collection

Review Chemistry, Organic

C-H functionalization of quinazolinones by transition metal catalysis

Prasanjit Ghosh et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

Add to Collection

Review Chemistry, Multidisciplinary

Intermolecular radical carboamination of alkenes

Heng Jiang et al.

CHEMICAL SOCIETY REVIEWS (2020)

Add to Collection

Review Chemistry, Multidisciplinary

Recent advances in copper-catalysed radical-involved asymmetric 1,2-difunctionalization of alkenes

Zhong-Liang Li et al.

CHEMICAL SOCIETY REVIEWS (2020)

Add to Collection

Article Chemistry, Organic

Visible-Light-Mediated Umpolung Reactivity of Imines: Ketimine Reductions with Cy2NMe and Water

Rui Wang et al.

ORGANIC LETTERS (2018)

Add to Collection

Article Chemistry, Multidisciplinary

A Toolbox Approach To Construct Broadly Applicable Metal-Free Catalysts for Photoredox Chemistry: Deliberate Tuning of Redox Potentials and Importance of Halogens in Donor-Acceptor Cyanoarenes

Elisabeth Speckmeier et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Add to Collection

Article Chemistry, Organic

Visible-Light Photoredox Catalyzed Oxidative/Reductive Cyclization Reaction of N-Cyanamide Alkenes for the Synthesis of Sulfonated Quinazolinones

Ping Qian et al.

ORGANIC LETTERS (2017)

Add to Collection

Article Chemistry, Organic

Metal-free sequential decarbonylative annulation of N-cyanamides for the construction of 2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-ones

Xueke Liu et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

Add to Collection

Article Chemistry, Applied

Copper-Catalyzed Divergent Trifluoromethylation/Cyclization of Unactivated Alkenes

Jing Zheng et al.

ADVANCED SYNTHESIS & CATALYSIS (2016)

Add to Collection

Article Chemistry, Multidisciplinary

Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals

Eleonora Fava et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Add to Collection

Review Biochemistry & Molecular Biology

Quinazolines and quinazolinones as ubiquitous structural fragments in medicinal chemistry: An update on the development of synthetic methods and pharmacological diversification

Imtiaz Khan et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2016)

Add to Collection

Article Chemistry, Multidisciplinary

Radical C-H functionalization to construct heterocyclic compounds

Jin-Tao Yu et al.

CHEMICAL COMMUNICATIONS (2016)

Add to Collection

Article Chemistry, Organic

Silver(I)-Mediated Phosphorylation/Cyclization Cascade of N-Cyanamide Alkenes for Divergent Access to Quinazolinones and Dihydroisoquinolinones

Jing Zheng et al.

ORGANIC LETTERS (2016)

Add to Collection

Review Chemistry, Organic

Advanced Synthetic Strategies for Constructing Quinazolinone Scaffolds

Rajendra S. Rohokale et al.

SYNTHESIS-STUTTGART (2016)

Add to Collection

Article Pharmacology & Pharmacy

Tryptanthrin Protects Hepatocytes against Oxidative Stress via Activation of the Extracellular Signal-Regulated Kinase/NF-E2-Related Factor 2 Pathway

Soo Young Moon et al.

BIOLOGICAL & PHARMACEUTICAL BULLETIN (2014)

Add to Collection

Article Biochemistry & Molecular Biology

Modeling in vitro inhibition of butyrylcholinesterase using molecular docking, multi-linear regression and artificial neural network approaches

Fang Zheng et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2014)

Add to Collection

Article Chemistry, Medicinal

Tricyclic Quinazoline Alkaloids: Isolation, Synthesis, Chemical Modification, and Biological Activity

Kh M. Shakhidoyatov et al.

CHEMISTRY OF NATURAL COMPOUNDS (2014)

Add to Collection

Article Chemistry, Organic

Synthesis of natural quinazolinones and some of their analogues through radical cascade reactions involving N-acylcyanamides

Marie-Helene Larraufie et al.

TETRAHEDRON (2013)

Add to Collection

Article Plant Sciences

Tryptanthrin inhibits Th2 development, and IgE-mediated degranulation and IL-4 production by rat basophilic leukemia RBL-2H3 cells

Kanso Iwaki et al.

JOURNAL OF ETHNOPHARMACOLOGY (2011)

Add to Collection

Article Chemistry, Multidisciplinary

Radical Synthesis of Guanidines from N-Acyl Cyanamides

Marie-Helene Larraufie et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Add to Collection

Article Chemistry, Multidisciplinary

Radical Migration of Substituents of Aryl Groups on Quinazolinones Derived from N-Acyl Cyanamides

Marie-Helene Larraufie et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Add to Collection

Review Chemistry, Organic

Radical reactions with 3H-quinazolin-4-ones:: synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin

W. Russell Bowman et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2007)

Add to Collection

Article Chemistry, Multidisciplinary

Radical cyclization of N-acylcyanamides: Total synthesis of luotonin A

Aurore Servais et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

Add to Collection

Article Chemistry, Medicinal

Privileged structure-based quinazolinone natural product-templated libraries: Identification of novel tubulin polymerization inhibitors

JF Liu et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2006)

Add to Collection

Article Chemistry, Medicinal

Synthesis and structure-activity relationships of vasicine analogues as bronchodilatory agents

Neeraj Mahindroo et al.

MEDICINAL CHEMISTRY RESEARCH (2005)

Add to Collection

Article Plant Sciences

Quantitative determination of the dual COX-2/5-LOX inhibitor tryptanthrin in Isatis tinctoria by ESI-LC-MS

H Danz et al.

PLANTA MEDICA (2002)

Add to Collection

© Peeref 2019-2024. All rights reserved.