Novel Synthesis of N-Phenyl-2-aminopyrimidine Derivatives under Solvent- Free Conditions (original) (raw)

Solventless convenient synthesis of new cyano-2-aminopyridine derivatives from enaminonitriles

Tetrahedron Letters, 2013

A synthesis of novel 4-substituted-3-cyano-2-aminopyridines using enaminonitriles and various primary amines was established under microwave irradiation and solvent-free conditions. Structures of the new compounds were characterized by IR, MS, 1 H and 13 C NMR data and the structure of 2-aminopyridine of the products was confirmed by X-ray analysis.

A Convenient Route for the Synthesis of 4-Aryl- and 4-Aminopyrimidines

Monatshefte f�r Chemie/Chemical Monthly, 2004

A series of ureidopropenenitriles were synthesised by Knoevenagel condensation of ArCOCH 2 CN and HC(OEt) 3 in presence of ureas in a one pot reaction. These ureidopropenenitriles were cyclised to 4-aryl-5-cyano-3-substituted pyrimidines (in acid) or to 4-amino-5-benzoylpyrimidines (in base) in 60-70% yields. The amine pyrimidine derivatives were further converted to substituted uracils by hydrolysis with isopentyl nitrite in DMF. Alkylation of uracils furnished 1,3-dimethyluracil derivatives with DMS in alkali. All new compounds were characterised by spectral and analytical methods.

Unexpected One-pot Synthesis of Novel 2-Aminopyrimidine-4-ones under Microwave Irradiation

Journal of the Chinese Chemical Society, 2014

One-pot, three-component condensation of guanidine, ethylbenzoylacetate and various aromatic aldehydes in the presence of NaHCO 3 have been investigated by microwave irradiation. The aromatic aldehydes bearing electron-withdrawing groups undergo condensation with guanidine and ethylbenzoylacetate to afford ethyl-2-amino-4-aryl-1,4-dihydro-6-phenylpyrimidine-5-carboxylate derivatives via Biginelli reaction. However, reaction of the aromatic aldehydes having electron-releasing groups with guanidine and ethylbenzoylacetate did not give the corresponding dihydropyrimidines. Instead, novel 2-amino-5-benzoyl-5,6-dihydro-6-arylpyrimidine-4(3H)-ones were obtained via an unexpected mechanism.

An eco-friendly and water mediated product selective synthesis of 2-aminopyrimidines and their in vitro anti-bacterial evaluation

A greener water mediated protocol for the efficient synthesis of a library of 2-amino-6-styryl pyrimidines (4) and their dihydro analogues (3) has been reported. Most of the saturated compounds (3) rather than their unsaturated analogues (4) showed better anti-bacterial (in vitro) activity against three human pathogens viz.Staphylococcus aureus, Klebsiella pneumoniaandEscherichia coli. In particular, three of them (3b, 3i&3k) exhibited high inhibition against the growth of all the three pathogens comparable with that of the reference drug, tetracycline.

A Facile Synthesis of 2-Amino-5-Cyano-4, 6-Disubstitutedpyrimidines under MWI Open Access

IJOC, 2011

Microwave Assisted Organic Synthesis (MAOS) is energy efficient and effective tool to speed up the synthesis for drug discovery process. In the present study we report a novel protocol for the rapid, high throughput synthesis of mononuclear 2-amino-5-cyano-4,6-disubstituted pyrimidines, adaptable to parallel synthesis for compound libraries. The overall reaction time in hrs has been reduced to 25-50 minutes with improved yields.

Critical Modification to Bulk Scale Synthesis of 2-Amino-5-carboethoxy-4-hydroxypyrimidine

Asian Journal of Chemistry

Our group reported pyrimidine derivatives as one of the first T-type calcium channel blockers [1,2]. The pyrimidine ring is pharmacologically important functional group especially in the broad fields of cardiovascular and psychotic drugs [3-5]. The pyrimidine group is recently been reported with numerous pharmacological applications emphasizing the direction of medicinal chemistry field and significance of heterocyclics [6-10]. Though it is believed that pyrimidines are less utilized as pharmacological synthons compared to other rings like dihydropyrimidine [11,12], pyridines [13,14], furons [15,16], thiophenes [17], thiazides [18], etc., the evolution of newer medicinal chemistry leads are limited [19]. This is because the pyrimidine synthesis reactions usually result in lower reactions yields compared to other heterocyclics [20,21]. The recent spurt in interest of pyrimidine compounds necessitates development of viable synthetic methods. A simple condensation reaction of acetoacetate or malonate with guanidine compound

Efficient Synthesis of 2-Aminopyridine Derivatives: Antibacterial Activity Assessment and Molecular Docking Studies

Molecules

A new and suitable multicomponent one-pot reaction was developed for the synthesis of 2-amino-3-cyanopyridine derivatives. Background: This synthesis was demonstrated by the efficient and easy access to a variety of substituted 2-aminopyridines using enaminones as key precursors under solvent-free conditions. Methods: A range of spectroscopic techniques was used to determine and confirm the chemical structures (FTIR, 1H NMR, 13C NMR). The antimicrobial potency of synthesized compounds (2a–d) was tested using disk diffusion assays, and the Minimum Inhibitory Concentration (MIC) for the active compounds was determined against a panel of microorganisms, including Gram-positive and Gram-negative bacteria and yeasts. Moreover, a docking analysis was conducted by Molecular Operating Environment (MOE) software to provide supplementary information about the potential, as well as an ADME-T prediction to describe the pharmacokinetic properties of the best compound and its toxicity. Results: T...