Convenient One-Pot Four-Component Synthesis of 6,8-Disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones via a Triple Mannich Reaction

2019 ◽  
Vol 72 (7) ◽  
pp. 542 ◽  
Author(s):  
Ahmed F. M. EL-Mahdy ◽  
Hassan A. H. El-Sherief ◽  
Zainab A. Hozien
Keyword(s):  
Reaction Mechanism ◽  
Functional Groups ◽  
Mannich Reaction ◽  
Spectroscopic Data ◽  
Atomic Charge ◽  
Secondary Amines ◽  
Primary Amines ◽  
One Pot ◽  
Elemental Analyses ◽  
Charge Calculations

An efficient and simple one-pot four-component protocol has been developed and performed for the synthesis of 6,8-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones, involving a triple Mannich reaction of 6-amino-2-(ethylthio)pyrimidin-4(3H)-one, formaldehyde, primary amines, and alcohols. Secondary amines were also utilised instead of alcohols as Mannich nucleophiles, and a variety of functional groups and electronically varied reaction partners were tolerated. This one-pot reaction facilitated the generation of a library of pyrimido[4,5-d]pyrimidin-4(3H)-ones in very good to excellent yields. The regioselectivity of this reaction was investigated using atomic charge calculations, and spectroscopic data confirmed that the triple Mannich products were 6,8-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones rather than the isomeric 3,6-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones. The structures of all compounds synthesised using the triple Mannich reaction were confirmed via spectroscopic and elemental analyses. The reaction mechanism was studied and confirmed by isolation of the intermediate.

scholarly journals A Single-Step Synthesis of Azetidine-3-Amines

2020 ◽  
Author(s):  
Brian J Wang ◽  
Matthew Duncton
Keyword(s):  
Functional Groups ◽  
Late Stage ◽  
Single Step ◽  
Secondary Amines ◽  
High Yield ◽  
Primary Amines ◽  
Privileged Structure ◽  
One Step ◽  
Alternative Procedures ◽  
Approved Drugs

<div> <p>The azetidine group is frequently encountered within contemporary medicinal chemistry where it is viewed as a privileged structure. However, the introduction of an azetidine can be synthetically challenging. Herein, a straight-forward one step synthesis of azetidine-3-amines, starting from a bench stable, commercial material is presented. The reaction tolerates functional groups commonly encountered in biological-, medicinal- and agro-chemistry, and proceeds in moderate-to-high yield with secondary amines, and moderate-to-low yield with primary amines. The methodology compares favorably to recent alternative procedures and can be utilized in “any-stage” functionalization, including late-stage azetidinylation of approved drugs and other compounds with pharmacological activity.</p> </div>

N-Acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides: highly selective and efficient reagents for acylation of amines in water

2016 ◽  
Vol 71 (2) ◽  
pp. 95-104 ◽  
Author(s):  
Sara Ebrahimi ◽  
Safoura Saiadi ◽  
Simin Dakhilpour ◽  
Seyed Nezamoddin Mirsattari ◽  
Ahmad Reza Massah
Keyword(s):  
High Stability ◽  
Solvent Free ◽  
Secondary Amines ◽  
Primary Amines ◽  
Green Solvent ◽  
One Pot ◽  
Selective Protection ◽  
Solvent Free Conditions ◽  
Aryl Amines ◽  
Acylation Reactions

AbstractA variety ofN-acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides (1a–e) were synthesized in one pot from 4-chloroaniline under solvent-free conditions and have been developed as chemoselective N-acylation reagents. Selective protection of primary amines in the presence of secondary amines, acylation of aliphatic amines in the presence of aryl amines, and monofunctionalization of primary-secondary diamines as well as selective N-acylation of amino alcohols using these reagents are described. All of the acylation reactions were carried out in water as a green solvent. High stability and easy preparation of these acylating reagents are other advantages of this method.

scholarly journals A new electrochemical strategy for the synthesis of a new type of sulfonamide derivatives

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Hamed Goljani ◽  
Zahra Tavakkoli ◽  
Ali Sadatnabi ◽  
Mahmood Masoudi-khoram ◽  
Davood Nematollahi
Keyword(s):  
Reaction Mechanism ◽  
Functional Groups ◽  
Disproportionation Reaction ◽  
Carbon Electrodes ◽  
One Pot ◽  
Electrochemical Generation ◽  
Type Reaction ◽  
Second Stage ◽  
Ping Pong ◽  
New Type

Abstract This study is the first report of electrochemical generation of hydroxyimino-cyclohexa-dien-ylidene haloniums and their application in the synthesis of new halo-N-hydroxysulfonamide derivatives. These compounds were obtained in a one-pot process based on the reaction of halonium acceptors with arylsulfinic acids. The method is easy to carry out, as it is performed using the carbon electrodes in a simple undivided cell. The protocol has a broad substrate scope with a tolerance for a variety of functional groups. The proposed mechanism is a ping-pong type reaction mechanism, which in its first stage the halonitroarene is reduced at the cathode to related hydroxylamine and in the second stage the cathodically generated hydroxylamine by oxidation at the anode and participating in disproportionation reaction is converted to the halonium acceptor.

One Pot Synthesis of 6-(4-carboxy-3-methyl-2-phenylquinolin-6-ylsulfonyl)-3-methyl-2-phenylquinoline-4-carboxylic Acids from Dapsone and α-ketobutyric Acid by a Doebner Reaction

2016 ◽  
Vol 40 (12) ◽  
pp. 715-717 ◽  
Author(s):  
Negar Moshref Javadi ◽  
Javad Azizian
Keyword(s):  
Biological Activity ◽  
Carboxylic Acids ◽  
Anticancer Agents ◽  
Spectroscopic Data ◽  
Aromatic Aldehydes ◽  
Reaction Conditions ◽  
One Pot ◽  
Promising Alternative ◽  
Elemental Analyses ◽  
Operational Simplicity

A series of new 6-(4-carboxy-3-methyl-2-phenylquinolin-6-ylsulfonyl)-3-methyl-2-phenylquinoline-4-carboxylic acids were synthesised by a one-pot reaction of dapsone, α-ketobutyric acid, and aromatic aldehydes in the presence of CuBr2 as a catalyst. Operational simplicity, mild reaction conditions, and eco-friendly procedure make this novel protocol a promising alternative for the preparation of quinoline-4-caboxylic acid derivatives. The structures of the products were established by elemental analyses and spectroscopic data. The biological activity of the new sulfone dimers was evaluated as having the potential for use as anticancer agents.

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.

One-pot amination of cyclohexanone-to-secondary amines over carbon-supported Pd: Unraveling the reaction mechanism and kinetics

2021 ◽  
Vol 417 ◽  
pp. 129236
Author(s):  
Luis E. Arteaga-Pérez ◽  
Raydel Manrique ◽  
Francisca Castillo-Puchi ◽  
Maray Ortega ◽  
Camila Bertiola ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Secondary Amines ◽  
One Pot ◽  
Mechanism And Kinetics ◽  
Supported Pd

scholarly journals Microwave-assisted synthesis of (aminomethylene)bisphosphine oxides and (aminomethylene)bisphosphonates by a three-component condensation

2016 ◽  
Vol 12 ◽  
pp. 1493-1502 ◽  
Author(s):  
Erika Bálint ◽  
Ádám Tajti ◽  
Anna Dzielak ◽  
Gerhard Hägele ◽  
György Keglevich
Keyword(s):  
Reaction Mechanism ◽  
Practical Method ◽  
Solvent Free ◽  
Secondary Amines ◽  
Primary Amines ◽  
Microwave Assisted Synthesis ◽  
Diphenylphosphine Oxide ◽  
Microwave Assisted ◽  
Reactant Pairs ◽  
By Products

A practical method was elaborated for the synthesis of (aminomethylene)bisphosphine oxides comprising the catalyst- and solvent-free microwave-assisted three-component condensation of primary amines, triethyl orthoformate and two equivalents of diphenylphosphine oxide. The method is also suitable for the preparation of (aminomethylene)bisphosphonates using (MeO)2P(O)H/(MeO)3CH or (EtO)2P(O)H/(EtO)3CH reactant pairs and even secondary amines. Several intermediates referring to the reaction mechanism together with a few by-products could also be identified.

scholarly journals Multicomponent Reactions, Solvent-Free Synthesis of 2-Amino-4-aryl-6-substituted Pyridine-3,5-dicarbonitrile Derivatives, and Corrosion Inhibitors Evaluation

2018 ◽  
Vol 2018 ◽  
pp. 1-9 ◽  
Author(s):  
Naglaa F. H. Mahmoud ◽  
Ahmed El-Sewedy
Keyword(s):  
Aromatic Aldehydes ◽  
Primary Amines ◽  
One Pot ◽  
Multicomponent Condensation ◽  
Wide Range ◽  
Elemental Analyses ◽  
High Yields ◽  
New Compounds ◽  
First Time ◽  
Solvent Free Synthesis

A number of 2-amino-4-aryl-6-substituted pyridine-3,5-dicarbonitrile derivatives were synthesized via one-pot multicomponent condensation reactions of different aromatic aldehydes with malononitrile and different primary amines, using different molecular ratios and different reaction conditions to achieve considerable product yields. Moreover, we succeed, for the first time to develop a new method to synthesize the aforementioned under the fusion condition without using solvent and catalysts. With this method, a wide range of novel 2-amino-3,5-dicyano-4-aryl-6-substituted aminopyridine derivatives were synthesized with high yields and board substrate of functional groups. The synthesized pyridine derivatives were found to have a corrosion inhibition efficiency, the rate of which increased with the increasing concentration of the derivatives. The structures of the new compounds were elucidated by spectroscopic data and elemental analyses.

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