Diastereoselective Dearomatization of Chalcone‐Based Quinolinium Salts to Assemble Bridged Quinobenzazepine Polycycles DOI Open Access

Chengxiang Luo,

Chaoyang Li, Lijie Zhang

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: unknown

Published: Sept. 13, 2023

Abstract Quinobenzazepines are useful in medicinal chemistry, but their synthesis is very challenging. Herein, we designed and synthesized a range of multi‐functional chalcone‐based quinolinium salts; synthetic application the rapid straightforward construction quinobenzazepines was successfully explored. A wide oxa‐bridged quinobenzazepine polycycles were afforded serendipitously through dearomative cascade reaction our newly developed salts acetylacetone. This strategy features high bond‐ ring‐forming efficiency complete regio‐ diastereoselective control.

Language: Английский

Recent advances in the dearomative functionalisation of heteroarenes DOI Creative Commons
Nicolas Kratena, Bruno Marinič, Timothy J. Donohoe

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(48), P. 14213 - 14225

Published: Jan. 1, 2022

This Perspective outlines the myriad of products that can be obtained by dearomatisation and functionalization heteroarene substrates. Complex 3D molecules often prepared in one step from simple arene starting materials.

Language: Английский

Citations

53

Base-Mediated Cascade Lactonization/1,3-Dipolar Cycloaddition Pathway for the One-Pot Assembly of Coumarin-Functionalized Pyrrolo[2,1-a]isoquinolines DOI
Qiang Tang, Yanan Liu,

Binbin Fei

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8420 - 8434

Published: June 5, 2024

An elegant and highly concise strategy for the construction of coumarin-functionalized pyrrolo[2,1-a]isoquinolines from available propargylamines isoquinolinium N-ylides has been disclosed. In this reaction, acted as a C2 synthon to form coumarin ring well 1,3-dipole construct pyrrole in single pot. This cascade process involves 1,4-conjugate addition/lactonization/1,3-dipolar cycloaddition four chemical bonds (one C–O bond three C–C bonds) two new heterocyclic skeletons. Additionally, most these compounds showed good fluorescence properties exhibited high molar extinction coefficient large Stokes shifts.

Language: Английский

Citations

6

Recent Progress in Gold‐Catalyzed Reactions of Alkynes for the Construction of Indole Frameworks DOI
Suven Das

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(8)

Published: June 21, 2023

Abstract Indole heterocycles hold an important position in chemical landscape because of their prominence natural products and pharmaceuticals. Consequently, development new efficient strategies to access indole scaffold are continuous interest. For the past few years, gold‐catalyzed activation alkyne has emerged as a powerful strategy for constructing heterocyclic skeleton. The present review highlights recent advances (2018–2023) toward synthesis skeletons via annulations alkynes. A variety alkynes, such as, ynamides, azido ortho ‐alkynyl anilines, propargylic alcohols, phenylimines, miscellaneous alkynes employed affording various architectures under gold catalysis. Moreover, mechanisms included most cases better understanding reaction pathway.

Language: Английский

Citations

15

The literature of heterocyclic chemistry, part XXII, 2022 DOI
Галина А. Газиева, Yu. B. Evdokimenkova, N. O. Soboleva

et al.

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0

Recent applications of 1,3-indanedione in organic transformations for the construction of fused- and spiro scaffolds DOI
Suven Das

Tetrahedron, Journal Year: 2022, Volume and Issue: 122, P. 132954 - 132954

Published: Aug. 9, 2022

Language: Английский

Citations

18

Indole frameworks via transition-metal-free annulation: a current perspective DOI
Suven Das

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(29), P. 13729 - 13775

Published: Jan. 1, 2023

The present review summarizes recent (2019–mid-2023) efforts towards the construction of indole core via transition-metal-free methods.

Language: Английский

Citations

10

One-pot C–N/C–C bond formation and oxidation of donor–acceptor cyclopropanes with tetrahydroisoquinolines: access to benzo-fused indolizines DOI
Pallab Karjee, Bijoy Debnath, Santu Mandal

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(30), P. 4068 - 4071

Published: Jan. 1, 2024

A two step one-pot annulation of donor–acceptor cyclopropanes with tetrahydroisoquinolines has been accomplished to furnish benzo-fused indolizines substrate scope and functional group diversity.

Language: Английский

Citations

3

Modular Assembly of Pyrrolo[3,4-c]isoquinolines through Rh-Catalyzed Cascade C–H Activation/Annulation of O-Methyl Aryloximes with Maleimides DOI

Yinsong Wu,

Yanan Liu,

Yangzilin Kong

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8447 - 8457

Published: June 4, 2024

An efficient and practical strategy for the construction of pyrrolo[3,4-

Language: Английский

Citations

3

Recent Applications of Quinolinium Salts in the Synthesis of Annulated Heterocycles DOI Creative Commons
Suven Das

SynOpen, Journal Year: 2022, Volume and Issue: 06(02), P. 86 - 109

Published: April 25, 2022

Abstract Quinoline derivatives are frequently found in natural products and biologically active compounds; however, construction of quinoline fused polyheterocycles is a challenging goal synthetic organic chemistry. In this regard, quinolinium salts meet the demand to great level, as they can be synthesized readily employed effectively for rapid condensed heterocyclic core. The present review focuses on recent (2015–2021) applications different salts, which react with suitable partners access diverse annulated products. Most reactions discussed here involve easily available starting materials, operationally simple, offer high atom-efficiency, environmentally benign. Mechanistic aspects representative transformations have also been highlighted better understand reaction pathways. 1 Introduction 2 Annulation Involving N-Alkyl Quinolinium Salts 2.1 Reaction Alkenes 2.2 Alkynes/Arynes 2.3 Phenolic Compounds 2.4 Cyclic/Acyclic Diketones 2.5 Amines/Cyclic Amines 2.6 Enamines 2.7 Isocyanoacetates 2.8 Cyclopropanes 2.9 Ring Expansion Reactions 3 Zwitterionic Tosylates 3.1 3.2 Allenes/Ketenes 3.3 Aldehyde-Amino Acid (Azomethine Ylide) 3.4 Sulfonium 3.5 Diazoacetate 4 Thiolates 4.1 4.2 Sulfenes 4.3 Arynes 5 N-Oxides 5.1 Diynes Ynones 5.2 Lactonization Acrylate 6 N-Iminoquinolinium 6.1 Allenoates 6.2 Hydroxymethylallyl Carbonate 7 Miscellaneous Cyclizations 8 Conclusions

Language: Английский

Citations

13

Metal-free photoinduced alkylative [3 + 2] annulation of terminal alkynes with N-alkyl isoquinolin-2-iums by catalytic isoquinoline-based electron donor–acceptor complex DOI

Ya‐Fei Han,

Yang Li, Xuan‐Hui Ouyang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(5), P. 1173 - 1181

Published: Jan. 1, 2023

Catalytic isoquinoline-based EDA complex photoreduced alkylative [3 + 2] annulation of alkynes with N -alkyl isoquinolin-2-iums toward pyrrolo[2,1- a ]isoquinolines is depicted.

Language: Английский

Citations

7