Facile Synthesis of New Imidazo[4',5':4,5]benzo[1,2-d] isoxazol-6-one Derivatives and In Silico Studies of Their Drug-like Profiles DOI
Maofeng Zhang,

Xing-Li Yan,

Lizhong Wang

et al.

Organic Preparations and Procedures International, Journal Year: 2021, Volume and Issue: 53(4), P. 413 - 421

Published: July 4, 2021

Heterocycles represent a crucial class of organic compounds, in part due to their numerous applications the field drug development. It was found that 85% 104 small molecule drugs appro...

Language: Английский

Recent developments and perspectives in the copper-catalyzed multicomponent synthesis of heterocycles DOI Creative Commons

Jaleel Fairoosa,

Mohan Neetha, Gopinathan Anilkumar

et al.

RSC Advances, Journal Year: 2021, Volume and Issue: 11(6), P. 3452 - 3469

Published: Jan. 1, 2021

Heterocycles are abundant in several pharmaceutical and naturally occurring compounds. Copper-catalyzed multicomponent reactions a convenient method for easy access to heterocycles. In this review, we focus on the advancement field past two years.

Language: Английский

Citations

54
Modular Assembly of Six‐Membered Carbocyclic Spirooxindoles via Peterson Olefination/Michael Addition/C(sp3) Arylation Cascade DOI
Feng‐Cheng Jia,

Zi‐Yi Yuan,

Na Luo

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(21), P. 2614 - 2620

Published: July 3, 2024

Comprehensive Summary Concise assembly of spirooxindoles is great significance but a challenging task in modern organic synthesis. Described herein an unusual base‐promoted [4+2] spiroannulation rarely used isatin‐derived β‐silylcarbinols with o ‐halogen aromatic ketones, which enables rapid and modular synthesis six‐membered carbocyclic high yields excellent functional group tolerance (> 50 examples). Mechanistic experiments revealed that this reaction involved Peterson olefination, Michael addition intramolecular C(sp 3 ) arylation cascade. The variegated synthetic derivatization target products successful construction bioactive molecules further illustrate the potential spirooxindole‐related drug discovery.

Language: Английский

Citations

4
Domino Sonogashira coupling/metal carbene-involved annulation enabled by Pd/Cu relay catalysis: rapid assembly of indazole-containing biheteroaryls DOI

Ruiming Ding,

Haili Cui,

Yongyan Zhu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(9), P. 2171 - 2176

Published: Jan. 1, 2023

An efficient and novel method has been developed for the synthesis of indazole-containing biheteroaryls via a domino Sonogashira coupling/azaenyne cycloisomerization/Barton–Kellogg reaction.

Language: Английский

Citations

8
Halocyclization of Olefinic 1,3-Dicarbonyls and Olefinic Amides in Aqueous Media Open in Air at Room Temperature DOI
Tingting Cao, Weikang Zhang,

Fu‐Hua Qin

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2020, Volume and Issue: 8(45), P. 16946 - 16951

Published: Nov. 4, 2020

A green and efficient procedure for the preparation of valuable 2,3-dihydrofurans benzoxazines has been achieved through halocyclization olefinic 1,3-dicarbonyls or amides. This protocol could be conducted under catalyst-, base-, oxidant-free conditions in aqueous media open to air at room temperature with good excellent yields. Notably, practicality this method is further highlighted by gram-scale reactions

Language: Английский

Citations

19
Decade Advances of NaN3 in Three‐component Reactions DOI
Zhan‐Yong Wang, Jiarong Li, Nan Wang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(5)

Published: April 10, 2023

Abstract Decade advances of sodium azide (2011–2022) have been summarized via mechanisms and target products. Sodium is commonly used as a nucleophile (N 3 − ) or radical source (⋅N in three‐component reactions. It's reactions with alkenes, alkynes, R−X (X=F, Cl, Br, I, OTs, B(OH) 2 , BF K, I + ArO Tf, N O SO ‐SiO other electrophiles will be discussed.

Language: Английский

Citations

5
Metal‐Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho‐Carbonyl Anilines DOI

Alankrita Garia,

Jatin Grover,

Nidhi Jain

et al.

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(29), P. 4125 - 4131

Published: July 19, 2021

Abstract Here, we report a metal‐free synthesis of anthranils from ortho ‐carbonyl anilines using PhIO as sole additive under ambient conditions. This methodology did not require any external additives and delivered in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in‐situ generation iminoiodane leading to nitrene subsequent nucleophilic attack oxygen aniline on results heterocyclization.

Language: Английский

Citations

10
Catalysed Aryl Amine Syntheses via Azides: From Azidation of Aryl Halides to Azide Reduction and Direct Amination DOI Creative Commons
Max Roemer

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

Published: May 6, 2024

Abstract This review summarises and discusses aryl amine azide syntheses from halides employing azides. The majority of the reported reactions proceed with copper catalysis or mediation. Often, an is formed in first step, which then reduced situ to a second step. occurrence reduction, depends on chosen reaction conditions substrates. formation only azides through Cu‐mediated C−N bond formations discussed, followed by mediated catalytic reduction different systems, azidation amines, viz . azidation‐amination strategies. allows for synthesis complex heterocycles multi‐step one‐pot procedures, several are summarised here. Examples application synthesising important amines employed as biologically active compounds, materials science also summarised. Finally, conducted control have been collected discussed combination mechanistic proposals. literature survey us pinpoint design criteria valuable includes choice such solvent system additives, involved metal promising

Language: Английский

Citations

1
TfOH-Promoted Decyanative Cyclization toward the Synthesis of 2,1-Benzisoxazoles DOI
Mengge Zhang, Yonggang Meng,

Yangang Wu

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(11), P. 7326 - 7332

Published: May 20, 2021

A novel solvent-free, TfOH-promoted decyanative cyclization approach for the synthesis of 2,1-benzisoxazoles has been developed. The reactions are complete instantly at room temperature and result in formation desired a 34–97% isolated yield.

Language: Английский

Citations

9
Merging Ullmann-type cyclization and ring-expansion: a facile assembly of pyrimidine-fused quinazolinones by copper catalysis DOI

Zhen-Wei Sun,

Xingqiang Lü,

Xiang Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(8), P. 2002 - 2006

Published: Jan. 1, 2023

A copper-catalyzed tandem cyclization reaction of readily available 4-bromoisatins and amidine hydrochlorides has been developed for the first time, enabling efficient synthesis pyrimidoquinazolinones in useful yields.

Language: Английский

Citations

3
Sodium Azide: An Inorganic Nitrogen Source for the Synthesis of Organic N‐Compounds DOI
Zahra Tashrifi,

Mohammad Mohammadi Khanaposhtani,

Bagher Larijani

et al.

ChemistrySelect, Journal Year: 2021, Volume and Issue: 6(47), P. 13419 - 13433

Published: Dec. 14, 2021

Abstract Sodium azide (NaN 3 ) is a colorless or white crystalline salt with diverse medicinal and industrial applications. Recently, NaN considered as an inexpensive valuable source of nitrogen in organic synthesis for the construction N ‐heterocycles, amines, nitriles amides due to extremely good nucleophilicity anion. Accordingly, can act single (a molecule transfer its azido group one atom) dual synthon (two molecules introduce two separate atoms, groups each) synthesis. However, although it has been extensively used there are rare reports on role synthon. In this review, we attempted summarize categorize recent literatures (from 2010 on) focusing use sodium usually via reductive amination brief concise description reaction mechanisms. respect, divided relevant database into main categories, namely The first category turn subcategories: (I) formation ‐heterocycles based number members rings (II) acyclic ‐compounds (primary amines/amides).

Language: Английский

Citations

7