scholarly journals From porphyrin benzylphosphoramidate conjugates to the catalytic hydrogenation of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin

2014 ◽  
Vol 10 ◽  
pp. 628-633 ◽  
Author(s):  
Marcos C de Souza ◽  
Leandro F Pedrosa ◽  
Géssica S Cazagrande ◽  
Vitor F Ferreira ◽  
Maria G P M S Neves ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Catalytic Hydrogenation ◽  
Fluorine Atom ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution

Three new porphyrin aminoalkyl dibenzylphosphoramidates were synthesized by nucleophilic aromatic substitution of onep-fluorine atom of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (TPPF20) by primary aminoalkyl dibenzylphosphoramidates. The nucleophilic aromatic substitution was promoted by microwave irradiation inN-methyl-2-pyrrolidinone. Attempts to remove the benzyl groups of the phosphoramidate moiety by hydrogenolysis with 10% Pd/C led to the cleavage of the P–N bond and the reduction of the macrocycle to hydroporphyrin-type derivatives. The extent of the effect of the catalytic hydrogenation toTPPF20with 10% Pd/C was then studied with a variety of solvents. The results showed that ethanol/DMF is the solvent of choice to produce chlorinTPCF20and an ethanol/DMF/NEt3mixture is more adequate to produce isobacteriochlorin (TPIF20).

Transition metal-free construction of trinuclear N-fused hybrid scaffolds by double nucleophilic aromatic substitution under microwave irradiation

2019 ◽  
Vol 21 (24) ◽  
pp. 6590-6593 ◽  
Author(s):  
Pham Duy Quang Dao ◽  
Ho-Jin Lim ◽  
Chan Sik Cho
Keyword(s):  
Transition Metal ◽  
Microwave Irradiation ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Metal Free ◽  
Green Construction ◽  
Free Construction ◽  
Hybrid Scaffolds

A green construction of trinuclear N-fused hybrid scaffolds by transition metal-free double C(sp2)–N coupling of 2-(2-bromoaryl)- and 2-(2-bromovinyl)benzimidazoles with 2-aminoazoles under microwave irradiation has been developed.

Novel nucleophilic aromatic substitution of the fluorine atom yielding a stable heptatrienide structure

2005 ◽  
Vol 54 (10) ◽  
pp. 2471-2472 ◽  
Author(s):  
Yu. G. Gololobov ◽  
O. A. Linchenko ◽  
Z. A. Starikova ◽  
I. A. Garbuzova ◽  
P. V. Petrovskii
Keyword(s):  
Fluorine Atom ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution

scholarly journals Microwave-assisted synthesis of azepines via nucleophilic aromatic substitution

2016 ◽  
Vol 81 (11) ◽  
pp. 1225-1230 ◽  
Author(s):  
Nina Bozinovic ◽  
Bogdan Solaja ◽  
Igor Opsenica
Keyword(s):  
Microwave Irradiation ◽  
Nucleophilic Aromatic Substitution ◽  
Irradiation Condition ◽  
Primary Amines ◽  
Microwave Assisted Synthesis ◽  
Aromatic Substitution ◽  
Microwave Assisted ◽  
Reaction Proceeds ◽  
Efficient Route

A novel and efficient route has been developed to afford 5H-dipyridoazepine derivatives from primary amines and 3,3'-(Z)-ethene-1,2-di-ylbis(4-chloropyridine). The procedure based on the double nucleophilic aromatic substitution provides a valuable synthetic tool for the synthesis of dipyridoazepines. The reaction proceeds without catalyst, under microwave irradiation condition.

scholarly journals Synthesis and nucleophilic aromatic substitution of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene

2016 ◽  
Vol 12 ◽  
pp. 192-197 ◽  
Author(s):  
Javier Ajenjo ◽  
Martin Greenhall ◽  
Camillo Zarantonello ◽  
Petr Beier
Keyword(s):  
Nucleophilic Substitution ◽  
Title Compound ◽  
Fluorine Atom ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Vicarious Nucleophilic Substitution ◽  
Direct Fluorination ◽  
Nitrogen Nucleophiles

3-Fluoro-5-nitro-1-(pentafluorosulfanyl)benzene was prepared by three different ways: as a byproduct of direct fluorination of 1,2-bis(3-nitrophenyl)disulfane, by direct fluorination of 4-nitro-1-(pentafluorosulfanyl)benzene, and by fluorodenitration of 3,5-dinitro-1-(pentafluorosulfanyl)benzene. The title compound was subjected to a nucleophilic aromatic substitution of the fluorine atom with oxygen, sulfur and nitrogen nucleophiles affording novel (pentafluorosulfanyl)benzenes with 3,5-disubstitution pattern. Vicarious nucleophilic substitution of the title compound with carbon, oxygen, and nitrogen nucleophiles provided 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzenes substituted in position four.

Novel Nucleophilic Aromatic Substitution of the Fluorine Atom Yielding a Stable Heptatrienide Structure.

ChemInform ◽  
2006 ◽  
Vol 37 (35) ◽  
Author(s):  
Yu. G. Gololobov ◽  
O. A. Linchenko ◽  
Z. A. Starikova ◽  
I. A. Garbuzova ◽  
P. V. Petrovskii
Keyword(s):  
Fluorine Atom ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution

scholarly journals Microwave Irradiation Assists the Synthesis of a Novel Series of bis-Arm s-Triazine Oxy-Schiff Base and Oxybenzylidene Barbiturate Derivatives

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2976
Author(s):  
Kholood Dahlous ◽  
Zainab Almarhoon ◽  
Ahmed-Yacine Badjah-Hadj-Ahmed ◽  
Zeid AL Othman ◽  
Ayman El-Faham
Keyword(s):  
Schiff Base ◽  
Microwave Irradiation ◽  
Acid Hydrazide ◽  
Thiobarbituric Acid ◽  
Nucleophilic Aromatic Substitution ◽  
Conventional Heating ◽  
Target Product ◽  
Aromatic Substitution ◽  
Benzaldehyde Derivatives ◽  
Yield And Purity

A novel series of s-triazines incorporating 4-hydroxybenzaldehyde and 4-hydroxy-3-methoxybenzaldehyde was prepared and fully characterized. The reaction was carried out via stepwise nucleophilic aromatic substitution of chlorine atoms in cyanuric chloride. The first chlorine was substituted by different amines (morpholine, piperidine, or diethylamine) to afford 2,4-dichloro-6-substituted-1,3,5-triazine. The second and third chlorines were substituted by benzaldehyde derivatives in the presence of Na2CO3 as a HCl scavenger to afford the target products: s-triazine oxyaldehyde derivatives (dipodal). The dipodal derivatives were reacted with acid hydrazide, hydralazine, barbituric, or thiobarbituric acid derivatives using conventional heating or microwave irradiation to afford the di-arm s-triazine oxy-Schiff base and oxybenzylidene barbiturate derivatives in good yields. Microwave irradiation done in less solvent afforded the target product in less reaction time with good yield and purity. These types of derivatives might have special interest in coordination and medicinal chemistry.

scholarly journals Machine learning meets mechanistic modelling for accurate prediction of experimental activation energies

2021 ◽  
Author(s):  
Kjell Jorner ◽  
Tore Brinck ◽  
Per-Ola Norrby ◽  
David Buttar
Keyword(s):  
Machine Learning ◽  
Activation Energies ◽  
Accurate Prediction ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Mechanistic Modelling

Hybrid reactivity models, combining mechanistic calculations and machine learning with descriptors, are used to predict barriers for nucleophilic aromatic substitution.

Enantioselective Nucleophilic Aromatic Substitution Reaction of Azlactones to Synthesize Quaternary α-Amino Acid Derivatives

Synlett ◽  
2020 ◽  
Author(s):  
Xiaohua Liu ◽  
Yi Li ◽  
Hao Pan ◽  
Wang-Yuren Li ◽  
Xiaoming Feng
Keyword(s):  
Hydrogen Bonding ◽  
Charge Transfer ◽  
Amino Acid ◽  
Substitution Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Amino Acid Derivatives ◽  
Amino Acid Esters ◽  
Aromatic Substitution ◽  
Charge Transfer Interaction ◽  
Acid Esters

AbstractAn asymmetric organocatalytic nucleophilic aromatic substitution reaction of azlactones with electron-deficient aryls was established. A variety of α-aryl α-alkyl α-amino acid esters and peptides were obtained in decent yields and stereoselectivities. A new bifunctional catalytic mode involving charge-transfer interaction and hydrogen bonding is proposed to explain the enantioselectivity.

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