Boron Lewis Acid Catalyzed Hydrophosphorylation of N-Heteroaryl-Substituted Alkenes DOI
Sarah Yunmi Lee,

Soojin Kwak,

Jeongin Choi

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 56(03), P. 399 - 407

Published: Nov. 28, 2023

Abstract The hydrophosphorylation of N-heteroaryl-substituted alkenes catalyzed by a boron Lewis acid catalyst is reported. This reaction occurs with range bearing N-heterocycles, including pyridines, quinoline, pyrrole, and benzothiazole, resulting in the production β-N-heteroaryl alkylphosphonates good yields under additive-free, operationally simple conditions. mechanistic insights suggest that this involves deprotonation P–H bond dialkyl phosphites, enabled cooperative effects basic N-heterocyclic moiety alkenes. phosphonate anion serves as an effective phosphorus nucleophile for conjugate addition to concurrently formed N-protonated These can be further converted into other valuable organophosphorus compounds through introduction alcohol group or reduction phosphine oxide moiety.

Language: Английский

Fluconazole Analogs and Derivatives: An Overview of Synthesis, Chemical Transformations, and Biological Activity DOI Creative Commons
Michał Janowski, Oleg M. Demchuk, Monika Wujec

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(12), P. 2855 - 2855

Published: June 15, 2024

Fluconazole (2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol), which was patented in 1981 and introduced for commercial use 1988, is a widely utilized antifungal drug whose mechanism of action involves inhibition the activity 14-α lanosterol demethylase. Its safety effectiveness have established it as one most frequently employed agents. Resistance to azole drugs becoming more common. It may be related mutation gene encoding enzyme. To address this issue, molecules with modifications three main regions fluconazole, namely hydroxyl group, aromatic ring, 1,2,4-triazole rings, been synthesized an attempt create potent drugs. These aim at enhancing against microorganisms improving pharmacokinetic parameters profiles compounds. The present review explores synthesis fluconazole derivatives, accompanied by insights into results biological studies evaluating therapeutic effects these

Language: Английский

Citations

5
Bromide-catalyzed oxo-amination of alkenes towards the synthesis of α-amine ketones under photoelectrocatalysis conditions DOI
Zhi‐Min Zong, Mingxu Wang, Xiaojing Zhao

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(13), P. 3525 - 3530

Published: Jan. 1, 2024

An efficient and novel bromide-catalyzed oxo-amination of aryl alkenes towards the synthesis α-amine ketones under photoelectrocatalysis conditions was developed. The generation 2-bromo-1-phenylethanone supposed as key step.

Language: Английский

Citations

3
High‐Energy Ball Milling Enables an Ultra‐fast Wittig Olefination Under Ambient and Solvent‐free Conditions DOI Creative Commons
Johanna Templ, Michael Schnürch

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(49)

Published: Aug. 29, 2024

Abstract 30 Seconds to success!—The Wittig reaction, a fundamental and extensively utilized reaction in organic chemistry, enables the efficient conversion of carbonyl compounds olefins using phosphonium salts. Traditionally, meticulous setup, including pre‐formation reactive ylide species via deprotonation salt, is crucial for achieving high‐yielding reactions under classical solution‐based conditions. In this report, we present an unprecedented protocol ultra‐fast mechanically induced solvent‐free ambient conditions, often eliminating need tedious strict air moisture exclusion. A range aldehydes ketones were reacted with diverse salts high‐energy ball milling frequently giving access respective only seconds.

Language: Английский

Citations

2
High‐Energy Ball Milling Enables an Ultra‐fast Wittig Olefination Under Ambient and Solvent‐free Conditions DOI Creative Commons
Johanna Templ, Michael Schnürch

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(49)

Published: Aug. 29, 2024

Abstract 30 Sekunden zum Erfolg! – Die Wittig‐Reaktion, eine grundlegende und weit verbreitete Reaktion in der organischen Synthesechemie, ermöglicht die effiziente Umwandlung von Carbonylverbindungen zu den entsprechenden Olefinen unter Verwendung Phosphoniumsalzen. Traditionell ist ein sorgfältiger Reaktionsaufbau, einschließlich vorangestellten Bildung einer reaktiven Ylid‐Spezies durch Deprotonierung eines Phosphoniumsalzes, entscheidend, um hohe Ausbeuten klassischen, lösungsmittelbasierten Bedingungen erzielen. In diesem Bericht stellen wir noch nie dagewesenes Protokoll für ultraschnelle mechanisch induzierte Wittig‐Reaktion lösungsmittelfreien vor, welches mühsame initiale Ylid‐Bildung striktem Luft‐ Feuchtigkeitsausschluss oft überflüssig macht. Eine Reihe Aldehyden Ketonen wurde mit verschiedenen Phosphoniumsalzen mittels hochenergetischem Kugelmahlen umgesetzt, wobei Olefine häufig nur zugänglich waren.

Citations

0
Five-membered ring systems: With more than 1 N atom DOI
Larry Yet

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 211 - 257

Published: Jan. 1, 2024

Language: Английский

Citations

0
Photoredox-Catalyzed C–H Methylation of N-Heteroarenes Enabled by N,N-Dimethylethanolamine DOI
Jiayang Wang, Yun Wang, Wei-Yang Lin

et al.

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

Published: Nov. 21, 2024

A visible-light-driven radical C-H methylation of

Language: Английский

Citations

0
Molecular-Oxygen-Mediated Multicomponent Oxidative Cyclization: Synthesis of Tertiary-Alcohol-Unit-Bearing N-Heterocycles via Transforming C–H to C–OH Bonds DOI

Xiaoshuang Guo,

Maozhong Miao, Peng Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 26, 2024

We developed a molecular-oxygen-mediated multicomponent oxidative cyclization strategy to synthesize N-heterocycles containing tertiary alcohol units via the formation of key C–OH bonds and quaternary carbon centers. This formal [3 + 2 1] annulation offers green sustainable alternative for de novo bond formation, using O2 as both oxidant oxygen source under metal- catalyst-free conditions. Notably, continuous [1,5]-hydrogen transfer together with excess alcohols promotes C–OH-bearing products. Additionally, generation centers inhibits conversion C═O bonds, thus stabilizing desired

Language: Английский

Citations

0
Oxoamination of Terminal Alkenes under Visible-Light-Induced Ruthenium Catalysis DOI
Martin Oestreich, Hendrik F. T. Klare, Aliyaah J. M. Rahman

et al.

Synfacts, Journal Year: 2023, Volume and Issue: 19(10), P. 0994 - 0994

Published: Sept. 14, 2023

Key words α-amino ketones - oxoamination photoredox catalysis ruthenium terminal alkenes

Language: Английский

Citations

0
Boron Lewis Acid Catalyzed Hydrophosphorylation of N-Heteroaryl-Substituted Alkenes DOI
Sarah Yunmi Lee,

Soojin Kwak,

Jeongin Choi

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 56(03), P. 399 - 407

Published: Nov. 28, 2023

Abstract The hydrophosphorylation of N-heteroaryl-substituted alkenes catalyzed by a boron Lewis acid catalyst is reported. This reaction occurs with range bearing N-heterocycles, including pyridines, quinoline, pyrrole, and benzothiazole, resulting in the production β-N-heteroaryl alkylphosphonates good yields under additive-free, operationally simple conditions. mechanistic insights suggest that this involves deprotonation P–H bond dialkyl phosphites, enabled cooperative effects basic N-heterocyclic moiety alkenes. phosphonate anion serves as an effective phosphorus nucleophile for conjugate addition to concurrently formed N-protonated These can be further converted into other valuable organophosphorus compounds through introduction alcohol group or reduction phosphine oxide moiety.

Language: Английский

Citations

0