Acid-Promoted Redox-Annulation toward 1,2-Disubstituted-5,6-dihydropyrrolo[2,1-α]isoquinolines: Synthesis of the Lamellarin Core DOI Creative Commons

Guo-Quan Hou,

Wenyan Zhao, Changjiang Deng

et al.

ACS Omega, Journal Year: 2022, Volume and Issue: 7(42), P. 37050 - 37060

Published: Oct. 14, 2022

An efficient synthesis of a variety 1,2-disubstituted-5,6-dihydropyrrolo[2,1-α]isoquinoline derivatives via an acid-promoted cyclization reaction between 1,2,3,4-tetrahydroisoquinoline (THIQ) and substituted α,β-unsaturated aldehyde is reported. This cycloaddition allows access to structurally diverse multisubstituted dihydropyrrolo[2,1-α]isoquinolines in moderate good yields, which was the core scaffold marine natural alkaloid lamellarins.

Language: Английский

Ruthenium(II)-Catalyzed C–C/C–N Coupling of 2-Arylquinazolinones with Vinylene Carbonate: Access to Fused Quinazolinones DOI
Zhaohui Wang, He Wang, Hua Wang

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(3), P. 995 - 999

Published: Jan. 27, 2021

In this work, ruthenium(II)-catalyzed C–C/C–N annulation of 2-arylquinazolinones with vinylene carbonate is reported to synthesize fused quinazolinones. This catalytic system tolerates a wide range substrates excellent functional-group compatibility. transformation, the acts as an ethynol surrogate without any external oxidant involved. Furthermore, preliminary mechanistic studies were conducted, and plausible cycle was also proposed.

Language: Английский

Citations

70

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

Anthranils: versatile building blocks in the construction of C–N bonds and N-heterocycles DOI Open Access
Yang Gao,

Jianhong Nie,

Yanping Huo

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(9), P. 1177 - 1196

Published: Jan. 1, 2020

This review article provides an overview of the recent progress in transformations anthranils, which have emerged as versatile building blocks assembly various C–N bonds and medicinally active heterocyclic systems.

Language: Английский

Citations

54

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

(NH4)2S2O8 promoted tandem radical cyclization of quinazolin-4(3H)-ones with oxamic acids for the construction of fused quinazolinones under metal-free conditions DOI
Shenyuan Gao, Menglu Cai, Gang Xu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(11), P. 2241 - 2251

Published: Jan. 1, 2024

A novel cascade radical addition/cyclization reaction of non-activated olefins and oxamic acids has been proposed.

Language: Английский

Citations

5

TFA/TBHP-promoted oxidative cyclisation for the construction of tetracyclic quinazolinones and rutaecarpine DOI
Feng‐Cheng Jia,

Tian-Zhi Chen,

Xiao‐Qiang Hu

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(13), P. 1635 - 1639

Published: Jan. 1, 2020

An efficient TFA/TBHP-promoted oxidative cyclisation of readily available isatins with 1,2,3,4-tetrahydroisoquinolines has been firstly developed. The potential utility this strategy was demonstrated by one-step synthesis a natural alkaloid Rutaecarpin.

Language: Английский

Citations

34

FeCl3/KI‐Catalyzed Tandem Oxidative Cyclization for Switchable Total Synthesis of Luotonin A, B and Derivatives DOI

Song Yingchun,

Ming‐Xuan Wang,

Yun‐Ying Yi

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1348 - 1355

Published: Jan. 13, 2024

Abstract A total synthesis strategy was developed for the of luotonin A, B and their analogues using synergistic FeCl 3 /KI‐catalyzed oxidative cyclization. This protocol utilizes cheap widely available N ‐propargyl 2‐methyl‐quinazolinones arylamines under mild conditions, it has a wide substrate scope high atom economy. Different natural products (luotonin derivatives) can be synthesized via unique switchable approach. Further transformations from to E structural modification demonstrate potential applications this method. Moreover, camptothecin also modified with reported afford hydroxyl‐substituted product.

Language: Английский

Citations

4

Structural Evidence for Aromatic Heterocycle N–O Bond Activation via Oxidative Addition DOI
Michael K. Bogdos, Patrick Müller, Bill Morandi

et al.

Organometallics, Journal Year: 2023, Volume and Issue: 42(3), P. 211 - 217

Published: Jan. 3, 2023

Many methods report the scission of N–O bonds aromatic heterocycles and their subsequent functionalization. Oxidative addition is one presumed pathways through which bond activation with transition metals achieved. We first well-defined pathway (benz)isoxazole's oxidative addition. also provide control experiments, show that may be broken by strong inorganic reductants. These results highlight are susceptible to both reduction addition, has important implications for catalysis. Exploring reactivity these complexes toward a series electrophiles leads discovery Staudinger-type β-lactam synthesis upon reaction ketene. Finally, we demonstrate choice different metal/ligand combinations allows selective into either C–I or in presence other.

Language: Английский

Citations

10

TBHP‐Mediated Oxidative Decarboxylative Cyclization in Water: Direct and Sustainable Access to Anti‐malarial Polycyclic Fused Quinazolinones and Rutaecarpine DOI
Nanjun Chen, Fei Xia, Yifan Zhao

et al.

Chinese Journal of Chemistry, Journal Year: 2020, Volume and Issue: 38(11), P. 1239 - 1244

Published: May 17, 2020

Summary of main observation and conclusion Polycyclic fused quinazolinones with anti‐malarial activity were synthesized through tert ‐butyl hydroperoxide (TBHP)‐mediated oxidative decarboxylative cyclization between commercially available isatins cyclic amines in one step. The reaction proceeds smoothly water without additional transition‐metal catalyst, acid base. newly products evaluated to exhibit moderate good against chloroquine drug‐sensitive Plasmodium falciparum 3D7 strain. Additionally, this method also provides direct approach Rutaecarpine yield.

Language: Английский

Citations

26

Copper‐Catalyzed Aerobic Oxidative Ring Expansion of Isatins: A Facile Entry to Isoquinolino‐Fused Quinazolinones DOI
Dahan Wang, Fuhong Xiao, Feng Zhang

et al.

Chinese Journal of Chemistry, Journal Year: 2020, Volume and Issue: 39(1), P. 87 - 92

Published: Aug. 4, 2020

A copper‐catalyzed aerobic oxidative ring expansion reaction of isatins with 1,2,3,4‐tetrahydroisoquinoline for the synthesis tetracyclic quinazolinones has been developed. This is performed smoothly under simple conditions to give corresponding products in moderate good yields functional group tolerance. The capacity resultant 5 H ‐isoquinolino[1,2‐ b ]quinazolin‐8(6 )‐one a range palladium‐catalyzed directing C—H activation further demonstrated, thus giving broader access diverse quinazolinones.

Language: Английский

Citations

21