Synthesis of N-heterocyclic compounds using N,N-dimethylacetamides as an electrophilic carbon source DOI
Dayoung Chun,

Seok Beom Lee,

Simin Chun

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(43), P. 8617 - 8624

Published: Jan. 1, 2024

In this study, N-heterocyclic compounds were synthesized using nitrogen-containing nucleophilic substrates and electrophilic carbon sources derived from

Language: Английский

Photodriven Radical-Polar Crossover Cyclization Strategy: Synthesis of Pyrazolo[1,5-a]pyridines from Diazo Compounds DOI
Peng Zhao, Yanbo Liu, Yuting Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2511 - 2516

Published: March 20, 2024

This work demonstrates the synthesis of a variety perfluoroalkyl heterocycles via visible-light-driven radical-polar crossover cyclization strategy. In this process, single-electron reduction/SNV-type/cyclization sequences follow radical addition reaction diazoester, which differs from current role diazoesters as precursors/acceptors. transformation excellent functional group compatibility and allows for modification many bioactive molecules with diazoesters. Such could represent novel approach to photochemical diazo compounds.

Language: Английский

Citations

18
Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction DOI

Yu‐Wei He,

Li Huang, Kun Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10854 - 10866

Published: July 12, 2024

A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing

Language: Английский

Citations

4
Condition‐Controlled Selective Synthesis of CF3‐Chromene and CF3‐Benzofuran from N‐Phenoxyacetamide and CF3‐Ynone DOI Open Access

Huihang Hou,

Shengnan Yan,

Yuanshuang Xu

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

Comprehensive Summary Presented herein is a condition‐controlled selective synthesis of CF 3 ‐chromene and ‐benzofuran based on the reaction N ‐phenoxyacetamide ‐ynone. When carried out in MeOH under catalysis Rh(III), formed via C—H metalation‐initiated alkenylation, acetamide group migration intramolecular oxo ‐nucleophilic addition. On other hand, when run DMSO promotion CsOAc, generated aza ‐Michael addition‐initiated [3,3]‐σ rearrangement, addition water elimination. To our knowledge, this first report construction chromene or benzofuran scaffold along with introduction unit from same starting materials. The methodology was scalable products could be readily transformed into valuable products. Moreover, thus obtained possess decent anticancer activity.

Language: Английский

Citations

0
Recent Advances in Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons DOI
Karthick Govindan, Alageswaran Jayaram,

Vijay Thavasianandam Seenivasan

et al.

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

Published: May 27, 2024

Abstract Nitrogen‐containing heterocycles represent fundamental components found in a myriad of natural compounds, pharmaceuticals, tailored bioactive substances, and agrochemicals. In recent decades, the field synthetic chemistry has prioritized these directing considerable research endeavour toward developing efficient concise methodologies for their synthesis. Consequently, there is growing interest pioneering novel approaches to fabricate immensely coveted structural motifs. Transition metal‐catalyzed reactions leveraging solvents as carbon (C1) synthons offer notable advantages, including streamlined processes, enhanced atom economy, environmental sustainability. This review sheds light on advancements utilization collective such methanol (alongside other alcohols), N,N ‐dimethylethanolamine (DMEA), triethylamine (TEA) (in conjunction with amines), tetrahydrofuran (THF), toluene, dichloromethane (DCM), dimethyl sulfoxide (DMSO), dimethylformamide (DMF) C1 synthons, serving foundational units synthesis N ‐heterocycles, quinazolinone, quinazoline, quinoxaline, pyridine, pyrimidine, among others. Various reaction conditions employing diverse transition metals, coupling partners, or reagents, reported literature, have been explored.

Language: Английский

Citations

2
Regioselective Annulation of 3(5)‐Aminopyrazole with Aryl Ketones or Aryl Alkynes Using <i>N</i>,<i>N</i>‐Dimethylethanolamine as a Single/Triple Carbon Synthon DOI

Xinyu Zhang,

Jing Chen,

Rener Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(17), P. 3591 - 3596

Published: June 19, 2024

Abstract An efficient and regioselective cyclization for construction of pyrazolo[3,4‐ b ]pyridines methylene‐bridged bis(pyrazolo[1,5‐ a ]pyrimidines) has been established. It involves [3+2+1] annulation 3(5)‐aminopyrazole, N,N ‐dimethylethanolamine (DMEA), with 1,2‐insertion aryl methyl ketones or 2,1‐insertion alkynes. DMEA is oxidized through C( sp 3 )‐H activation to provide single triple carbon source.

Language: Английский

Citations

1
Eco-Friendly alpha,beta-C(sp3)-H Difunctionalization of Tertiary Amines via Sequential [1,5]-Hydride Transfer and Hetero-Diels-Alder Cyclization DOI
Yi Zhang, Huihui Yan, Peng Zhao

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(77), P. 10712 - 10715

Published: Jan. 1, 2024

An unprecedented eco-friendly multi-component domino reaction for the synthesis of novel

Language: Английский

Citations

1
Synthesis of N-heterocyclic compounds using N,N-dimethylacetamides as an electrophilic carbon source DOI
Dayoung Chun,

Seok Beom Lee,

Simin Chun

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(43), P. 8617 - 8624

Published: Jan. 1, 2024

In this study, N-heterocyclic compounds were synthesized using nitrogen-containing nucleophilic substrates and electrophilic carbon sources derived from

Language: Английский

Citations

1