Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN DOI Creative Commons
Joseph Dean,

Natalia Buckler Reinoso,

Francesco Spiedo

и другие.

Reactions, Год журнала: 2024, Номер 5(4), С. 812 - 822

Опубликована: Ноя. 1, 2024

Flow chemistry has shown significant versatility over the last two decades, offering advantages in efficiency, scalability, and sustainability. In this study, continuous stirred tank reactor (CSTR) was used to optimise synthesis of α-hydroxyphosphonates via Pudovik reaction their subsequent conversion phosphates through phospha-Brook rearrangement. The study highlights that using CSTRs allows for better control parameters, leading reduced times improved yields compared traditional batch methods. optimised conditions successfully facilitated a range organophosphates, including electron-rich electron-poor derivatives, with high efficiency. Additionally, one-pot tandem process combining rearrangement developed, reducing hours while maintaining comparable yields. This work demonstrates potential flow synthesising complex organophosphorus compounds, achieving higher shorter times, highlighting effectiveness methodologies.

Язык: Английский

Catalyst- and solvent-free coupling of 2-methyl quinazolinones and 3-(trifluoroacetyl)coumarins: An environmentally benign access of quinazolinone derivatives DOI Creative Commons

Xiaodan Chang,

Liangxin Fan, Lijun Shi

и другие.

Journal of Saudi Chemical Society, Год журнала: 2023, Номер 27(2), С. 101621 - 101621

Опубликована: Фев. 25, 2023

An environmentally benign highly atom-economic protocol for the construction of CC bond has been developed under catalyst- and solvent-free conditions. This involves efficient coupling 2-methyl quinazolinones with 3-(trifluoroacetyl)coumarins access quinazolinone derivatives in excellent yields (up to 90 %). The crystal structure compound 3di was investigated by X-ray diffraction analysis. biological activities, such as vitro antifungal activity against Fusarium graminearum, moniliforme, oxysporum, Phytophthora parasitica var nicotianae, Rhizoctonia solani Kuhn, were investigated. bioassay results indicated that most target products exhibited promising fungicidal 3 cl 95 % R. solani, an EC50 value 10.6 μg/mL.

Язык: Английский

Процитировано

6
Green synthesis of 2-trifluoromethyl quinoline derivatives under metal-free conditions and their antifungal properties DOI Creative Commons
Liangxin Fan,

Fangyu He,

Lijun Shi

и другие.

Journal of Saudi Chemical Society, Год журнала: 2023, Номер 27(6), С. 101761 - 101761

Опубликована: Окт. 27, 2023

The skeleton of 2-trifluoromethyl quinoline is the core structure many natural products and pharmaceutical molecules. synthesis this scaffold limited by metal catalysis, harsh conditions, toxic or hazardous reagents solvents, lower atom-economy. Herein, a novel method for quinolines via [4+2] cyclization β-keto esters 1,3-diketones with various substituted o-aminobenzaldehydes using free catalyst in EOH reported. This atom- step-economical protocol features simple operation, broad substrate scope, good functional-group compatibility. synthetic utility methodology was highlighted easy gram-scale late-stage functionalization, which would promote vigorous development chemistry. Moreover, vitro antifungal activities against F. graminearum (from wheat), corn), moniliforme, oxysporum, R. solani were investigated to further potential these compounds.

Язык: Английский

Процитировано

5
Design, Catalyst-Free Synthesis of New Novel α-Trifluoromethylated Tertiary Alcohols Bearing Coumarins as Potential Antifungal Agents DOI Creative Commons

Shengfei Jiang,

Guoyu Yang, Lijun Shi

и другие.

Molecules, Год журнала: 2022, Номер 28(1), С. 260 - 260

Опубликована: Дек. 28, 2022

A new method for the synthesis of α-trifluoromethylated tertiary alcohols bearing coumarins is described. The reaction 3-(trifluoroacetyl)coumarin and pyrrole provided target compounds with high yields under catalyst-free, mild conditions. crystal structure compound 3fa was investigated by X-ray diffraction analysis. biological activities, such as in vitro antifungal activity against Fusarium graminearum, oxysporum, moniliforme, Rhizoctonia solani Kuhn, Phytophthora parasitica var nicotianae, were investigated. bioassay results indicated that 3ad, 3gd, 3hd showed broad-spectrum vitro. Compound 3cd exhibited excellent fungicidal an EC50 value 10.9 μg/mL, which comparable to commercial triadimefon (EC50 = 6.1 μg/mL). Furthermore, molecular docking study suggested had binding affinities 1W9U, like argifin.

Язык: Английский

Процитировано

6
Highly Chemoselective Synthesis of Azaarene-Equipped CF3-Tertiary Alcohols under Metal-Free Conditions and Their Fungicidal Activities DOI Creative Commons

Bingyi Zhou,

Guoyu Yang,

Caixia Wang

и другие.

ACS Omega, Год журнала: 2022, Номер 7(42), С. 38084 - 38093

Опубликована: Окт. 10, 2022

A highly chemoselective reaction between α,β-unsaturated trifluoromethyl ketones with azaarenes under metal-free conditions was carried out, affording a range of valuable azaarene-equipped CF3-tertiary alcohols in moderate to excellent yields (up 95% yield) good tolerance functional groups, and their structures were confirmed by NMR, HRMS, X-ray diffraction for validation. This method features simple (only solvent), high atom- step-economy, broad substrate scope. Moreover, most the target products exhibited promising fungicidal activities, compound 3al 91.65% activity against R. solani, an EC50 value 0.18 mg/mL.

Язык: Английский

Процитировано

5
Room Temperature DBN Initiated Phospha‐Brook Rearrangement of α‐Hydroxyphosphonates to Phosphates DOI Creative Commons

Muskaan Mahandru‐Gill,

Aleema Iqbal,

Margarita Damai

и другие.

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(43)

Опубликована: Окт. 14, 2022

Abstract A series of substituted aryl phosphate esters have been synthesized from their α‐hydroxyphosphonates substrates, using DBN (1,5 diazabicyclo(4.3.0)non‐5‐ene) at room temperature, via a phospha‐Brook rearrangement. The aryl‐substrate dependence the rearrangement was explored, and excellent yields were achieved irrespective whether moiety activated or unactivated. plausible mechanism for has proposed. Based on low temperature 31 P‐NMR, is proposed to take place an oxaphosphirane intermediate.

Язык: Английский

Процитировано

4
A one-pot approach to novel α-trifluoromethylated coumarin-bearing tertiary alcohols promoted by CH3COOH/NH4OAc via consecutive ring-opening/aldol sequence DOI Creative Commons
Lulu Wu, Zhenliang Pan, Liangxin Fan

и другие.

Journal of Saudi Chemical Society, Год журнала: 2022, Номер 27(1), С. 101578 - 101578

Опубликована: Дек. 9, 2022

A one-pot two-step reaction of 2-(trifluoromethyl)-2-hydroxy-2H-chromene with aryl ketone afforded α-trifluoromethylated tertiary alcohols bearing coumarins. The atomic economic and simply manipulative involved premier treatment mixtures CH3COOH NH4OAc in process. proceeded to give the title compounds moderate good yields.

Язык: Английский

Процитировано

3
Green synthetic approaches in organophosphorus chemistry: recent developments DOI
Goutam Brahmachari

Royal Society of Chemistry eBooks, Год журнала: 2024, Номер unknown, С. 287 - 298

Опубликована: Фев. 21, 2024

Organophosphorus chemistry is a broad and exciting field, with potential opportunities for researchers involved in multi-disciplinary areas of scientific endeavour, including organic, medicinal, pharmaceutical, agricultural, industrial chemistry. compounds find extensive applications all these fields owing to their inherent physical biological properties. Since its first development the 90s, green sustainable has grown considerably over past two decades. It become much more prevalent among working branches chemical science. As part noteworthy developments, synthetic organic chemists have been motivated develop eco-friendly methodologies generating phosphorus-functionalised interest, focusing on various principles. result, considerable progress towards accomplished during last decade. In continuation our earlier contributions, this chapter also aims offer an overview such developments approaches organophosphorus reported 2021.

Язык: Английский

Процитировано

0
Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN DOI Creative Commons
Joseph Dean,

Natalia Buckler Reinoso,

Francesco Spiedo

и другие.

Reactions, Год журнала: 2024, Номер 5(4), С. 812 - 822

Опубликована: Ноя. 1, 2024

Flow chemistry has shown significant versatility over the last two decades, offering advantages in efficiency, scalability, and sustainability. In this study, continuous stirred tank reactor (CSTR) was used to optimise synthesis of α-hydroxyphosphonates via Pudovik reaction their subsequent conversion phosphates through phospha-Brook rearrangement. The study highlights that using CSTRs allows for better control parameters, leading reduced times improved yields compared traditional batch methods. optimised conditions successfully facilitated a range organophosphates, including electron-rich electron-poor derivatives, with high efficiency. Additionally, one-pot tandem process combining rearrangement developed, reducing hours while maintaining comparable yields. This work demonstrates potential flow synthesising complex organophosphorus compounds, achieving higher shorter times, highlighting effectiveness methodologies.

Язык: Английский

Процитировано

0