An Oxidant-Free and Mild Strategy for Quinazolin-4(3H)-One Synthesis via CuAAC/Ring Cleavage Reaction DOI Creative Commons

Yueling He,

Zhong‐Tao Yang,

Danyang Luo

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(15), P. 5734 - 5734

Published: July 28, 2023

An oxidant-free and highly efficient synthesis of phenolic quinazolin-4(3H)-ones was achieved by simply stirring a mixture 2-aminobenzamides, sulfonyl azides, terminal alkynes. The intermediate N-sulfonylketenimine underwent two nucleophilic additions the group eliminated through power aromatization. natural product 2-(4-hydroxybenzyl)quinazolin-4(3H)-one can be synthesized on large scale under mild conditions with this method.

Language: Английский

Catalyst-free photoinduced radical sulfonylation/cyclization of unactivated alkenes toward sulfone-containing quinazolinones DOI
Siyuan Chen,

Ying-Shan Wang,

Xian Han

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(4), P. 1169 - 1174

Published: Dec. 29, 2023

A catalyst-free, photoinduced three-component reaction involving sulfur dioxide insertion/sulfonyl radical addition to an unactivated CC double bond/Minisci-type cyclization sequence has been developed access sulfonated quinazolinones.

Language: Английский

Citations

8

Cascade Cyclization of N-Cyanamide Alkenes for the Divergent Synthesis of Azido-, Nitro-, and Alkenyl-Containing Pyrroloquinazolinones DOI
Bo Jiang, Cui Zhang,

Tai‐Gang Fan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(38), P. 8028 - 8033

Published: Sept. 16, 2024

Radical cascade cyclizations of

Citations

3

Recent advances in radical thiocyanation cyclization or spirocyclization reactions DOI

Qinqin Yan,

Shiliu Chen,

Jie Fan

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(46), P. 9112 - 9122

Published: Jan. 1, 2023

Organic thiocyanates are valuable biological moities and drug-building blocks. They can also transform effectively into thioethers, thiols, alkynyl thiocarbamates in synthetic chemistry. With respect to the merits of thiocyanates, many chemists our research team have developed diverse strategies access SCN-revised heterocycles/spirocycles via an effective radical cyclization process. Hence, this review article first describes importance/application thiocyanates. Subsequently, it summarizes reaction conditions, substrate scopes, plausible mechanism, respectively, excellent work stated above.

Language: Английский

Citations

6

Acid-catalyzed radical tandem alkylation/cyclization of unactivated alkenes with ketones: Access to ketoalkyl-substituted quinazolinone derivatives DOI

Jian-Li Wu,

Meng Yan,

Lulu Fan

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 162, P. 134085 - 134085

Published: June 11, 2024

Language: Английский

Citations

2

Visible‐Light Induced Trifluoromethylation/Cyclization of Unactivated Alkene‐Bound Quinazolinones DOI

Luqian Zou,

Hengyuan Zhao,

Xinming Wang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(17)

Published: March 19, 2024

Abstract Herein, we reported a selective, mild method for the visible‐light‐photocatalyzed trifluoromethylation and cyclization of unactivated tethered alkenes to provide tri‐ tetracyclic quinazolinones. Trifluoroacetic acid anhydride are inexpensive readily available reagents process that proceeds without addition strong oxidant. The wide substrate scope formation 5‐ 6‐membered rings demonstrated in 44–82 % yields. Control experiments basis proposed mechanism involving photocatalyzed SET from fac ‐Ir(ppy) 3 TFAA trifluoromethyl radical‐mediated regioselective cyclization. practicality protocol was illustrated by gram‐scale synthesis 76 yield.

Language: Английский

Citations

1

Photocatalytic alkenes to ring-fused quinazolin-4(3H)-ones via proton-transfer shuttle using TFA DOI
Xianming Wang,

Xinhan Li,

Luqian Zou

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 158, P. 133990 - 133990

Published: April 11, 2024

Language: Английский

Citations

1

Photoredox/HAT-Catalyzed Intramolecular Hydrocyclization of Alkenes toward 2,3-Fused Quinazolinones and Dihydroquinazolinones DOI
Dong Li, Xiaoqing Wang,

Yanhui Gou

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 2, 2024

New photochemical approaches to 2,3-fused quinazolinones and dihydroquinazolinones are disclosed. The intramolecular hydrocyclization proceeds in moderate excellent yields across diverse alkenes with high regioselectivity diastereocontrol. Mechanistic studies indicated that the radical cascade processes involve thiophenol acting as single-electron transfer hydrogen atom reagents. success of gram-scale synthesis proves strategy can be used for practical applications.

Language: Английский

Citations

1

Metal-Free Photoredox Intramolecular Cyclization of N-Aryl Acrylamides DOI Open Access
Zhao‐Sheng Liu, Xiaochen Ji, Feng Zhao

et al.

Catalysts, Journal Year: 2023, Volume and Issue: 13(6), P. 1007 - 1007

Published: June 14, 2023

A novel metal-free photoredox-catalyzed cyclization reaction of N-aryl acrylamide is herein reported that provides synthetically valuable oxindole derivatives through the bis-mediation H2O and aldehyde. In this work, sustainable visible light was used as energy source, organic light-emitting molecule 4CzIPN served efficient photocatalyst. The main characteristics are environmentally friendly high yields.

Language: Английский

Citations

1

Photocatalyzed Acylmethylation/Cyclization of Unactivated Alkenes with Sulfoxonium Ylides towards Acylmethylated Polycyclic Quinazolinones DOI

Yechun Wu,

Lingli Liu, Jin‐Tao Yu

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: May 16, 2024

Abstract The synthesis of acylmethylatated pyrrolo‐quinazolinones was developed via photo‐induced cascade radical addition/cyclization N ‐(but‐3‐enyl)quinazolin‐4(3 H )‐ones with sulfoxonium ylides using 4CzIPN as the photocatalyst. This approach also suitable for construction piperidino‐quinazolinones. protocol features mild conditions, convenient operation, broad substrate scope and good functional group compatibility.

Language: Английский

Citations

0

Visible-light-induced selective hydrolipocyclization and silylation of alkenes: access to ring-fused quinazolin-4(3H)-ones and their silicon-substituted derivatives DOI
Shoucai Wang, Ziren Chen, Fei Xue

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(21), P. 6019 - 6025

Published: Jan. 1, 2024

A visible-light-induced intermolecular silylation and hydrolipocyclization using hydrosilane as the hydrogen silicon source has been developed, which provided an efficient pathway for synthesis of organosilanes polycyclic quinazolinones.

Language: Английский

Citations

0