RESUMEN

This manuscript reports on the synthesis and characterization of a new polymeric copper complex ([Cu3(DMAP)8(µ3-CO3)2]I2) n ·xH2O and its successful application in C-O and C-S cross coupling reactions for the synthesis of biologically important phenoxypyrimidine and arylthiopyrimidine scaffolds. In an attempt to synthesize [Cu(DMAP)4I]I by adopting a procedure reported by Roy et al. with slight modification, the authors discovered a new polymeric Cu-complex that contains µ3-CO3 bridges. The polymeric linear structure of the complex was established using single crystal X-ray analysis. FT-IR, UV-vis and DSC studies were also performed on the polymeric complex. This novel polymeric Cu-complex was found to efficiently catalyse C-O/C-S cross coupling reactions between chloropyrimidines and phenols/thiophenols in an aqueous medium within a short reaction time, delivering their corresponding phenoxypyrimidines and arylthiopyrimidines. Using this protocol, 22 phenoxypyrimidines and 6 arylthiopyrimidines were successfully synthesized. The synthesized novel compounds were well characterized using 1H and 13C NMR spectroscopy and HRMS analysis and were screened for their drug-likeness properties using the SwissADME webtool.

RESUMEN

This letter describes the first synthetic methodology for phenoxypyrimidines that avoids the direct use of phenols or their salts. In contrast to the general trend of delivering Suzuki-Miyaura cross-coupling products in reactions between aryl or alky halides and arylboronic acids, the substrate pairs used herein (chloropyrimidines and arylboronic acids) led to C-O bond formation under the reaction conditions. In total, 25 phenoxypyrimidines were successfully synthesized using the described protocol, 6 of which had a structural resemblance to etravirine.

Asunto(s)

Ácidos Borónicos , Cobre , Ácidos Borónicos/química , Catálisis , Cobre/química , Estructura Molecular , Sales (Química)

RESUMEN

A one pot two step methodology for the synthesis of ten derivatives of 5-arylpyrrolo[2,3-d]pyrimidine has been reported. The methodology exploits the strong reducing nature of alkaline Na2S2O4 solution coupled with favorability of Michael type addition reaction in alkaline medium. The methodology demands attraction as it is non-catalytic, quite general for wide range of nitrostyrenes and possesses comprehensive advantages over most of the earlier methods in terms of reaction time as well as yield. The methodology enjoys additional advantage of utilizing cheaper and easily available chemicals as reagent for the purpose. Some of the synthesized compounds are found to possess remarkable activity against some of the tested bacterial strains.

Asunto(s)

Antibacterianos/síntesis química , Pirimidinas/química , Pirroles/química , Antibacterianos/química , Antibacterianos/farmacología , Cristalografía por Rayos X , Ciclización , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Conformación Molecular , Pirimidinas/síntesis química , Pirimidinas/farmacología , Pirroles/síntesis química , Pirroles/farmacología

RESUMEN

BACKGROUND: Synthesis of oximes is an important reaction in organic chemistry, because these versatile oximes are used for protection, purification, and characterization of carbonyl compounds. Nitriles, amides via Beckmann rearrangement, nitro compounds, nitrones, amines, and azaheterocycles can be synthesised from oximes. They also find applications for selective α-activation. In inorganic chemistry, oximes act as a versatile ligand.Several procedures for the preparation of oximes exist, but, most of them have not addressed the green chemistry issue. They are associated with generation of pollutants, requirement of high reaction temperature, low yields, lack of a generalized procedure, etc. Hence, there is a demand for developing an efficient, convenient, and non-polluting or less polluting alternative method for the preparation of oximes. In this context, bismuth compounds are very useful as they are cheap in general, commercially available, air stable crystalline solids, safe, and non-toxic, hence easy to handle. RESULTS: Carbonyl compounds (aliphatic, heterocyclic, and aromatic) were converted into the corresponding oximes in excellent yields by simply grinding the reactants at room temperature without using any solvent in the presence of Bi2O3. Most importantly, this method minimizes waste disposal problems, provides a simple yet efficient example of unconventional methodology and requires short time. CONCLUSIONS: We have developed a novel, quick, environmentally safe, and clean synthesis of aldoximes and ketoximes under solvent-free grinding condition.

RESUMEN

The title compound, C(19)H(21)ClN(6)O(4), is a 1:2 adduct of p-chloro-benzaldehyde and uracil. It crystallizes with two mol-ecules in the asymmetric unit. The two uracil units in the same mol-ecule are connected by a pair of strong N-H⋯O hydrogen bonds. The packing is stabilized by N-H⋯O, C-H⋯O and C-H⋯N inter-actions.