Suzuki-Miyaura coupling under microwave enhanced conditions: synthesis of 2-(hetero)aryl benzimidazoles

Abstract

An expedient, palladium-mediated cross-coupling approach to functionalize the benzimidazole-based core under microwave-assisted conditions has been developed and is described. This protocol, which incorporates appendage diversity on this potential scaffold, is found to be compatible with a wide range of electronicallyand sterically-divergent (hetero)aryl boronic acids. The use of the PdCl 2 /(SPhos) catalytic system allows the formation of a stable and highly active LPd(0) species which was found to be critical for the successful synthesis of these novel, pharmacologically-relevant molecules.

A modified approach for the synthesis of biologically relevant 5-substituted-2-N-aryl-1,3-oxazole derivatives in mild conditions

“…We then decided to treat the intermediate 3b with different primary and secondary amines 4a-h in view of synthesizing more decorated oxazole based target molecules. Microwave irradiation reactions are always considered to be superior to conventional heating methodologies owing to its rapid product formation with lesser side-products [14][15][16][17][18][19][20]. Accordingly, we decided to utilize microwave irradiation for the synthesis of our target molecules.…”

Towards novel tacrine analogues: Pd(dppf)Cl2·CH2Cl2 catalyzed improved synthesis, in silico docking and hepatotoxicity studies

“…Recent advancements in this field have further allowed the incorporation of diverse frameworks in a biologically relevant core leading to the generation of complex molecular architectures. 6 …”

Efficient one pot preparation of novel 1-oxo-3-aryl-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-2-carboxylic acid derivatives in a green solvent

“…14 Because the benzo [4,5]imidazo [1,2-a]pyridine scaffold show interesting biological activities, the synthesis of this group of compounds has been realised via several routes, including cycloaddition reactions, 6,9,15 condensation reactions, [16][17][18] multicomponent reactions, 10,[19][20][21][22][23] and multistep approaches. 5,[24][25][26] Also, metallic and non-metallic catalysts, [27][28][29][30] microwave irradiation, 31 and a series of transition metal catalysts have been used for the preparation of these compounds. 1,32 No doubt, the existing methods are useful, but also possess certain limitations such as an extended reaction time, special apparatus, high temperature, expensive catalysts, toxic solvents, and tedious workup processes.…”