Photo‐Triggered Self‐Induced Homolytic Dechlorinative Sulfonylation/Cyclization of Unactivated Alkenes: Synthesis of Quinazolinones Containing a Sulfonyl Group DOI
Bin Sun, Hao Ding,

Hai‐Xia Tian

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 364(4), P. 766 - 772

Published: Nov. 24, 2021

Abstract A self‐photocatalyzed sulfonylation/cyclization of quinazolinones containing unactivated alkenes with various sulfonyl chlorides was developed. The protocol provides access to radicals via energy transfer from the quinazolinone skeleton chloride. Notably, transformations proceeded without any external photocatalysts, additives, or oxidants, providing an alternative method for fabricating sulfonylated compounds. magnified image

Language: Английский

Electrophotocatalytic tri- or difluoromethylative cyclization of alkenes DOI
Danna Chen,

Xuege Yang,

Dongyin Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(10), P. 2482 - 2490

Published: Jan. 1, 2023

Photoelectrocatalysis is mild yet potent and this work unlocks the potential of unactivated alkenes for oxidant-free oxidative cyclization alkenes.

Language: Английский

Citations

33

Radical-mediated photoredox hydroarylation with thiosulfonate DOI

Xiaoyuan Wan,

Dahan Wang, Huawen Huang

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(19), P. 2767 - 2770

Published: Jan. 1, 2023

Radical-mediated photoredox hydroarylation reaction of unactivated alkenes using thiosulfonate compounds as key radical precursors to synthesize pyridyquinazolinone and pyrroloquinazolinone derivatives is described.

Language: Английский

Citations

23

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

Zixian Yang,

Xian Wu,

Jie Zhang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(10), P. 1683 - 1688

Published: March 8, 2023

A visible-light-induced hydrocyclization of unactivated alkenes was developed using 3CzClIPN as the photocatalyst to generate substituted α-methyldeoxyvasicinones and α-methylmackinazolinones in moderate good yields. An intermolecular hydrogen atom transfer with THF source involved. Mechanism studies indicated that intramolecular addition situ formed aminal radical alkene generated polycyclic quinazolinone.

Language: Английский

Citations

23

Photoredox streamlines electrocatalysis: photoelectrosynthesis of polycyclic pyrimidin-4-ones through carbocyclization of unactivated alkenes with malonates DOI

Minglin Tao,

Feng Qin,

Kaixing Gong

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(7), P. 4199 - 4208

Published: Jan. 1, 2024

A new photoelectrocatalytic mode permits the synthesis of polycyclic pyrimidin-4-ones through dehydrogenative cyclization malonates with unactivated alkenes.

Language: Английский

Citations

15

Photoinduced EDA Complexes Enabled Radical Tandem Cyclization/Arylation of Unactivated Alkene with 2-Amino-1,4-naphthoquinones DOI
Bin Sun,

Xiayue Shi,

Xiaohui Zhuang

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(5), P. 1862 - 1867

Published: Feb. 19, 2021

A visible-light-induced radical tandem cyclization/arylation between 2-amino-1, 4-naphthoquinone and N-allyl-2-bromo-2,2-difluoroacetamides has been developed without an external photocatalyst. The transformation could be carried out at room temperature gave a variety of C-3-functionalized 2-amino-1,4-naphthoquinone derivatives in moderate to excellent yields. Moreover, mechanistic studies revealed that the reaction is driven by formation electron donor–acceptor (EDA) complex.

Language: Английский

Citations

52

Selective oxidation of alkenes to carbonyls under mild conditions DOI
Jun Xu, Yilan Zhang, Xiao‐Guang Yue

et al.

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(15), P. 5549 - 5555

Published: Jan. 1, 2021

This study demonstrates a photo-induced and tetrahydrofuran (THF)-based radical strategy for the selective oxidation of alkenes to carbonyls using O2 as sole oxidant water solvent.

Language: Английский

Citations

49

Rapid alkenylation of quinoxalin-2(1H)-ones enabled by the sequential Mannich-type reaction and solar photocatalysis DOI
Lin Huang, Jun Xu, Lei He

et al.

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 32(11), P. 3627 - 3631

Published: April 21, 2021

Language: Английский

Citations

41

Electrosynthesis of CF3‐Substituted Polycyclic Quinazolinones via Cascade Trifluoromethylation/Cyclization of Unactivated Alkene DOI
Lei Liu,

Wangqin Zhang,

Chao Xu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(7), P. 1319 - 1325

Published: Feb. 23, 2022

Abstract An atom and step economy cascade trifluoromethylation/cyclization of unactivated alkene with Langlois reagent as a CF 3 source is described. A variety polycyclic quinazolinones were successfully synthesized in 52–81% yields under transition metal‐ oxidant‐free conditions. The used this strategy possesses the advantages bench‐stablity, cost‐effectivity high‐efficiency. Additionally, gram‐scale reaction, broad substrate scope good functional group tolerance demonstrated synthetic usefulness protocol. magnified image

Language: Английский

Citations

36

Revisiting aromatic diazotization and aryl diazonium salts in continuous flow: highlighted research during 2001–2021 DOI
Jianli Chen,

Xiaoxuan Xie,

Jiming Liu

et al.

Reaction Chemistry & Engineering, Journal Year: 2022, Volume and Issue: 7(6), P. 1247 - 1275

Published: Jan. 1, 2022

Aryl diazonium salts play an important role in chemical transformations; however their explosive nature limits applications batch.

Language: Английский

Citations

32

Recent advances in the synthesis of 2,3-fused quinazolinones DOI

Wang Wang,

Pei‐Sen Zou,

Li Pang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(32), P. 6293 - 6313

Published: Jan. 1, 2022

As one of the most important structural units in pharmaceuticals and medicinal chemistry, quinazolinone its derivatives exhibit a wide range biological pharmacological activities, including anti-inflammatory, antitubercular, antiviral, anticancer etc. In particular, 2,3-fused quinazolinones have attracted much attention because rings fused to 2,3-positions improve their rigidity planarity. Their synthetic strategies made great advances recent years. Therefore, this review focuses on novel for synthesis from 2017 2022, such as difunctionalization alkenes, ring-opening easily available small rings, dehydrogenative cross-coupling reactions, transition-metal catalyzed cyclizations, cycloadditions, other cascade reactions.

Language: Английский

Citations

30