scholarly journals Room-Temperature, Base-Mediated Selective Synthesis of 2-(Arylamino)ethanols and 2-Aryloxyethanols

SynOpen ◽  
2019 ◽  
Vol 03 (04) ◽  
pp. 124-137 ◽  
Author(s):  
Rahul B. Sonawane ◽  
Swapnali R. Sonawane ◽  
Nishant K. Rasal ◽  
Sangeeta V. Jagtap
Keyword(s):  
Functional Groups ◽  
Aromatic Amines ◽  
Room Temperature ◽  
Alkyl Halide ◽  
Selective Synthesis ◽  
Formal Synthesis ◽  
Mild Conditions ◽  
Primary Aromatic Amines

A simple and efficient protocol for base-mediated selective synthesis of 2-(arylamino)ethanols from primary aromatic amines and 2-aryloxyethanols from phenols, promoted by K2CO3 has been achieved under mild conditions. Even in presence of excess alkyl halide, selective mono-N-alkylation has been achieved. Tolerance of a variety of functional groups is demonstrated by 15 examples of selective N-alkylation of aromatic amines and 19 examples of O-alkylation of phenols. The efficacy of the protocol is demonstrated by the formal synthesis of Ticlopidine­®, Vildagliptin®, Quetiapine®, and Gemfibrozil®.

scholarly journals Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles

2020 ◽  
Vol 2020 ◽  
pp. 1-9
Author(s):  
Hassan Kabirifard ◽  
Pardis Hafez Taghva ◽  
Hossein Teimouri ◽  
Niloofar Koosheshi ◽  
Parastoo Javadpour ◽  
...  
Keyword(s):  
High Temperature ◽  
Carbonyl Group ◽  
Aromatic Amines ◽  
Room Temperature ◽  
Organic Ligands ◽  
Carboxyl Group ◽  
Primary Aromatic Amines

The reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-butenamides 2–5, while that with naphthylamines and 1,3-phenylenediamine in ethanol at high temperature led to 5-phenylamino-2,5-dihydrothiophene-2-ones 6–8 as organic ligands in the medium to good yields. These showed the nucleophilic attacks of N-nucleophiles, except primary aromatic amines, on thioester carboxyl group (C-2) of thiophene-2,3-dione ring 1. However, the nucleophilic attacks of primary aromatic amines on the carbonyl group (C-3) of thiophene-2,3-dione 1 occurred in the form of substituted thiophenes.

scholarly journals High Performance Redox Initiating Systems Based on the Interaction of Silane with Metal Complexes: A Unique Platform for the Preparation of Composites

Molecules ◽  
2020 ◽  
Vol 25 (7) ◽  
pp. 1602
Author(s):  
Ahmad Arar ◽  
Haifaa Mokbel ◽  
Frédéric Dumur ◽  
Jacques Lalevée
Keyword(s):  
Metal Complexes ◽  
Aromatic Amines ◽  
High Performance ◽  
Room Temperature ◽  
Hazardous Substances ◽  
Gel Time ◽  
Chemical Mechanisms ◽  
Mild Conditions ◽  
Spin Resonance ◽  
Methacrylate Monomers

Currently, Redox Initiating Systems (RISs) of Free Radical Polymerization (FRP) are mainly based on the interaction of aromatic amines with peroxides (e.g., dibenzoyl peroxide (BPO)) that can be both toxic and unstable. In the present work, we aim to replace these hazardous substances in new RIS that can be peroxide-free and amine-free. Our redox two components (2K) initiating system is based on diphenylsilane (DPS) as reducing agent combined with different metal complexes (Mn(acac)2, Cu(AAEMA)2 or Fe(acac)3) as oxidizing agents. For the new proposed RIS, an excellent reactivity is found for the polymerization of benchmark methacrylate monomers under mild conditions (redox polymerization done under air and at room temperature); remarkably, it is also possible to finely control the gel time. Different techniques (optical pyrometry, Real-Time FTIR spectroscopy, Cyclic Voltammetry and Electron Spin Resonance (ESR)) were used to follow the polymerization processes but also to shed some light on the new redox chemical mechanisms.

Cerium(IV) Tetrabutylammonium Nitrate (CTAN): A Mild and Efficient N-dearylation Agent for Synthesis of N-unsubstituted 2-azetidinones

2017 ◽  
Vol 41 (4) ◽  
pp. 246-249 ◽  
Author(s):  
Maaroof Zarei
Keyword(s):  
Functional Groups ◽  
Room Temperature ◽  
Mild Conditions ◽  
Tetrabutylammonium Nitrate

A simple and efficient protocol for the conversion of N-p-methoxyphenyl, N-p-ethoxyphenyl, N-p-methoxynaphthyl, N-3,4-dimethoxybenzyl and N-p-methoxybenzyl-2-azetidinones to N-unsubstituted 2-azetidinones using cerium(IV) tetrabutylammonium nitrate (CTAN) in dichloromethane is described. The method is compatible with a number of functional groups, and N-unsubstituted 2-azetidinones can be prepared under mild conditions at room temperature. The reaction is rapid, and pure products are obtained in good yields.

The Reaction of 2-(Acylamino)benzonitriles with Primary Aromatic Amines: A Convenient Synthesis of 2-Substituted 4-(Arylamino)quinazolines

Synthesis ◽  
2015 ◽  
Vol 47 (11) ◽  
pp. 1623-1632 ◽  
Author(s):  
Elina Marinho ◽  
M. Proença
Keyword(s):  
Acetic Acid ◽  
Trifluoroacetic Acid ◽  
Aromatic Amines ◽  
Room Temperature ◽  
Ethyl Chloroformate ◽  
Convenient Synthesis ◽  
Primary Aromatic Amines

2-Substituted 4-(arylamino)quinazolines were prepared from 2-(acylamino)benzonitriles and primary arylamines by refluxing in either ethanol using trifluoroacetic acid as a catalyst or acetic acid. The 2-aminobenzonitrile was acylated by reaction with anhydrides, isocyanates, or ethyl chloroformate at room temperature.

A Selective and Versatile Synthesis of Substituted Chromones via Addition of Phenols to Dimethyl Acetylenedicarboxylate

1995 ◽  
Vol 48 (3) ◽  
pp. 677 ◽  
Author(s):  
MJ Stoermer ◽  
DP Fairlie
Keyword(s):  
Functional Groups ◽  
Addition Reaction ◽  
Initial Step ◽  
High Yield ◽  
Selective Synthesis ◽  
Dimethyl Acetylenedicarboxylate ◽  
Substituted Phenols ◽  
Valuable Component ◽  
Mild Conditions ◽  
Wide Range

Despite many published syntheses of chromones, none has been reported to be both selective for chromones and tolerant of ring substitution. The addition of substituted phenols to dimethyl acetylenedicarboxylate is now reported as a versatile high yield initial step in a simple three-step synthesis of chromone 2-carboxylic acids. Triethylamine being used to deprotonate the substituted phenol, the addition to dimethyl acetylenedicarboxylate proceeds under mild conditions and tolerates a wide range of functional groups on the phenol. Although not stereoselective, both fumarate and maleate aryloxy products of this addition can then be cyclized, according to a known method, to chromones without contamination by isomeric coumarins. Thus the addition reaction is a valuable component of a versatile and selective synthesis of substituted chromones.

A Convenient One-Pot Synthesis of Pyrazolo[3,4-d]pyrimidines and s-Triazolo[3,4-b][1,3,5]thiadiazines

1997 ◽  
Vol 52 (11) ◽  
pp. 1401-1412 ◽  
Author(s):  
Zeinab A. Hozien ◽  
Abd El-Wareth A. O. Sarhan ◽  
Hassan A. H. El-Sherief ◽  
Abdalla M. Mahmoud
Keyword(s):  
Mannich Reaction ◽  
Aromatic Amines ◽  
Good Yield ◽  
Room Temperature ◽  
Secondary Amines ◽  
One Pot ◽  
Aminomethyl Derivatives ◽  
Primary Aromatic Amines ◽  
The Mannich Reaction ◽  
Primary Aliphatic Amines

Abstract The reaction of 5-amino-3-aryl-1-phenylpyrazoles (1a-d) with formaldehyde and secondary amines in boiling ethanol gave the corresponding 4-alkylaminomethyl derivatives (2a-f) and bis-(4-pyrazolyl)methane (4a,b) as byproduct. Such reaction with primary aliphatic and aro­ matic amines at room temperature afforded 1,3,5-trisubstituted (5a-h) and 1,3.5,7-tetrasubstituted tetrahydropyrazolo[3,4-d]pyrimidines (8a-k) respectively in good yield. Similarily, the Mannich reaction of 5-mercapto-3-phenyl-1,2,4-triazole (9) with secondary amines, in boiling ethanol, and primary aromatic amines, at room temperature, gave 2 -substituted aminomethyl derivatives (10a-c) and (14a-g) respectively,while with primary aliphatic amines, p-toluidine and p-anisidine,at room temperature,and with other primary aromatic amines, in boiling ethanol, afforded the cyclized products 12,4-triazolo[3,4-b]thiadiazines (13a-e); (15f,g) and (15a-e), respectively.

Rearrangements in the Furan Series. II. The Reaction Between Furfuraldehyde and Aromatic Amines

1979 ◽  
Vol 32 (5) ◽  
pp. 1079 ◽  
Author(s):  
KG Lewis ◽  
CE Mulquiney
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Room Temperature ◽  
Furan Series ◽  
Mineral Acids ◽  
Primary Aromatic Amines ◽  
Stable Structures

A survey of the reaction of a variety of primary aromatic amines with furfuraldehyde has shown that, in most cases, the product isolated has the 2,4-diarylaminocyclopent-2-enone structure as established in the case of aniline. In a number of cases the products were shown to be the isomeric 4,5-diarylamino derivatives. It has been established that the 2,4-diarylamino derivatives are the more stable structures and that 4,5-disubstituted isomers are intermediates. Treatment of the 4,5-diarylaminocyclopent-2-enones with mineral acids gives a facile ring opening at room temperature to form the corresponding Stenhouse salt. A mechanism is suggested for both the above reactions. The results of some previous work are clarified.

Copper-Mediated Synthesis of Monofluoro Aryl Acetates via Decarboxylative Cross-Coupling

Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2886-2890 ◽  
Author(s):  
Anis Fahandej-Sadi ◽  
Rylan Lundgren
Keyword(s):  
Functional Groups ◽  
Building Block ◽  
Room Temperature ◽  
Cross Coupling ◽  
Mild Conditions ◽  
Aryl Bromides

We report the Cu-promoted oxidative cross-coupling of α-fluoromalonate half-esters and aryl boron reagents to deliver mono­fluoro α-aryl acetates under mild conditions (in air at room temperature). The reaction uses a simple, readily available monofluorinated building block to generate arylated compounds with functional groups that are not easily tolerated by existing methods, such as aryl bromides, iodides, pyridines, and pyrimidines.

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