Synthesis of Triazatriphenylene Derivative Through Multi‐Component Reaction of Aryl‐amine, Aldehyde, and Alkyne DOI Open Access

Sachie Yamamoto,

Naruki Ishida,

Takeshi Yasuda

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(7)

Published: May 23, 2023

Abstract The Povarov reaction is a representative multicomponent used for synthesizing nitrogen‐containing aromatic compounds from amines, aldehydes, and dienophiles, such as electron‐rich alkenes alkynes. In this study, we investigated triple of 1,3,5‐triaminobenzne with aldehydes phenylacetylene to obtain triazatriphenylene derivatives. Reactions arylaldehydes containing electron‐donating groups proceeded smoothly provide contrast, reactions electron‐withdrawing resulted in low yields. are probably more favorable terms high stability imine intermediates smooth electrophilic cyclization. Single‐crystal X‐ray structure analysis revealed that the aryl derived had small dihedral angles between core. derivative tertiary butyl ( tBu‐TaT ) glass transition temperature, while without H‐TaT lower highest occupied molecular orbital (HOMO) lowest unoccupied (LUMO) level served an efficient hole‐blocking material better electron transport properties than those . This study provides insights into scope limitations based on reaction, substituent dependence crystal structures, physical π‐extended compounds.

Language: Английский

Rongalite as C1 Synthon in the Synthesis of Divergent Pyridines and Quinolines DOI
Huan Gao,

Liyun Zhou,

Jie‐Ping Wan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7188 - 7198

Published: May 12, 2023

Rongalite has been used as a cheap and efficient carbon synthon for the synthesis of divergent N-heteroaromatics, including different pyridines quinolines. The selective products can be achieved by employing enaminones or enaminones/anilines reaction partners. In addition, compared with using conventional aldehyde synthons, rongalite displays an evident advantage in providing considerably higher product yields under milder conditions. GC-MS analysis process performed to probe possible mechanism.

Language: Английский

Citations

32

Six‐Membered Aromatic Nitrogen Heterocyclic Anti‐Tumor Agents: Synthesis and Applications DOI
Jiatong Li,

Ao Gu,

Xiao‐Mei Nong

et al.

The Chemical Record, Journal Year: 2023, Volume and Issue: 23(12)

Published: Nov. 27, 2023

Cancer stands as a serious malady, posing substantial risks to human well-being and survival. This underscores the paramount necessity explore investigate novel antitumor medications. Nitrogen-containing compounds, especially those derived from natural sources, form highly significant category of agents. Among these, agents with six-membered aromatic nitrogen heterocycles have consistently attracted attention chemists pharmacologists. Accordingly, we present comprehensive summary synthetic strategies clinical implications these compounds in this review. entails an in-depth analysis synthesis pathways for pyridine, quinoline, pyrimidine, quinazoline. Additionally, historical progression, targets, mechanisms action, effectiveness small molecule inhibitors possessing structural features.

Language: Английский

Citations

17

Metal-free assembly of diverse polysubstituted pyridines via an efficient cascade approach using tertiary enaminones and α,β-unsaturated sulfonylketimines DOI
Xiang Li, Qiwen Pang, Yang Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2607 - 2612

Published: Jan. 1, 2024

A metal-free, scalable, and cascade protocol for assembling diverse polysubstituted pyridines from tertiary enaminones α,β-unsaturated sulfonylketimines by cleaving C–N/N–S bonds is reported.

Language: Английский

Citations

4

Selective 6π‐Electrocyclization of N‐Vinyl‐α,β‐Unsaturated Nitrones to Prepare Polysubstituted Pyridine Derivatives DOI Open Access

Li‐Yao Ding,

Yan‐Jiao Lu,

Jung-Hyun Pang

et al.

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

Published: March 7, 2025

Comprehensive Summary Herein, we have developed a facile method for the synthesis of various polysubstituted pyridine derivatives through selective 6π‐electrocyclization N ‐vinyl‐ α , β ‐unsaturated nitrones. It was found that gold catalysts promoted carbon‐6π‐electrocyclization nitrones to afford 6‐alkenyl ‐oxides in 43%—75% yields, whereas copper facilitated oxygen‐6π‐electrocyclization give 6‐epoxy pyridines 41%—83% yields. The present features broad substrate scope, good functional group tolerance, high cyclization selectivity, and diversity scaffolds.

Language: Английский

Citations

0

Preparation of Highly‐Substituted Pyridines via Diels‐Alder Reactions of Vinylallenes and Tosyl Cyanide DOI
Nathan H. Faialaga, Christian Gomez,

Samuel G. Bartko

et al.

Organic Syntheses, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 25

Published: Aug. 1, 2024

Abstract This chapter presents the procedure for preparation of highly‐substituted pyridines via Diels‐Alder reactions vinylallenes and tosyl cyanid. The procedures in Organic Syntheses are intended use only by persons with proper training experimental organic chemistry. All hazardous materials should be handled using standard work chemicals described references such as “Prudent Practices Laboratory”. development practical efficient methods construction highly substituted remains a challenging goal synthesis. Vinylallenes reactive dienes which engage cycloadditions triple bonds to afford isoaromatic products that isomerize aromatic systems spontaneously or under mild conditions. authors have developed several strategies synthesis based on nitrogen heterodienophiles. also describes optimal conditions reaction vinylallene 2 cyanide.

Language: Английский

Citations

0

One-pot Synthesis of Substituted Pyridines from Alkyl Ketones and Enamines by the Nickel-catalyzed Dehydrogenation of Alkyl Ketones DOI Open Access
Satoshi Ueno,

Ryohei Maeda,

Yuya Kogure

et al.

Chemistry Letters, Journal Year: 2023, Volume and Issue: 52(3), P. 148 - 151

Published: Jan. 25, 2023

The one-pot synthesis of substituted pyridines from alkyl ketones, Stork enamines, and ammonia is reported. This reaction involves the nickel-catalyzed dehydrogenation ketone conjugate addition enamine, followed by condensation with an ammonium salt to yield corresponding pyridine. Furthermore, α-alkylation δ-amino-γ,δ-unsaturated intermediates leads tetrasubstituted pyridine in excellent yields means a three-step reaction.

Language: Английский

Citations

1

Six-membered ring systems: pyridines and benzo derivatives DOI

Jeanese C. Badenock

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 383 - 425

Published: Jan. 1, 2023

Language: Английский

Citations

1

Synthesis, evaluation of biological activity and SAR of new thioalkyl derivatives of pyridine DOI
Sh. Sh. Dashyan, Eugene V. Babaev, A. G. Ayvazyan

et al.

Bioorganic Chemistry, Journal Year: 2024, Volume and Issue: 148, P. 107435 - 107435

Published: May 8, 2024

Language: Английский

Citations

0

Crystal structures, Hirshfeld surface analysis, antimicrobial activity, and optical properties based on DFT calculations of two new organic-inorganic hybrids: [nClBzPy]2[MnCl4] (n = 2, 4) DOI
Shiyu Hu, Yan Jiang,

Bao-Yi Hu

et al.

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1313, P. 138694 - 138694

Published: May 21, 2024

Language: Английский

Citations

0

Polysubstituted Pyridines from 1,4-Oxazinone Precursors DOI Creative Commons

L. C. Thompson,

Adrianne M. Kinsey,

Zannatul Shahla

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 12, 2024

This study describes a general method for the preparation of 1,4-oxazin-2-one intermediates from acetylene dicarboxylate and β-amino alcohol precursors. Oxazinones prepared in this manner were employed tandem cycloaddition/cycloreversion reaction sequence with model alkyne (phenyl acetylene) to give substituted pyridine products. Fundamental reactivity selectivity studies are complemented by synthesis polycyclic ergot alkaloid natural product xylanigripone A.

Language: Английский

Citations

0