Sharma Poonam, Mehara Pushkar, Das Pralay
Chemical Technology Division, CSIR- Institute of Himalayan Bioresource Technology, Palampur, 176061, H.P, India.
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India.
Chem Asian J. 2023 Mar 14;18(6):e202201288. doi: 10.1002/asia.202201288. Epub 2023 Feb 17.
Herein, we demonstrated heterogeneous and recyclable polystyrene-supported palladium (Pd@PS) nanoparticles (NPs) catalyzed tandem addition and intramolecular aminocarbonylative cyclization approach for the synthesis of potentially bioactive 2-(alkylamino/amino)-3-arylquinazolin-4(3H)-one analogues from 2-iodophenylcarbodiimides employing amines as nucleophiles and oxalic acid as an ex-situ CO alternative. Various cyclic/acyclic primary and secondary amines were employed and selectively produced substituted 2-(alkylamino)-3-arylquinazolin-4(3H)-ones in good to excellent yields. In addition, we extended the developed strategy to fix two ammonium carbamate and oxalic acid as gaseous NH and CO sources respectively, for the synthesis of 2-amino-3-arylquinazolin-4(3H)-one derivatives. Furthermore, gram scale applicability, diverse substrate scope and high recyclability of the Pd@PS catalyst were the major achievements of the developed protocol.
在此，我们展示了一种由多相且可回收的聚苯乙烯负载钯（Pd@PS）纳米颗粒（NPs）催化的串联加成和分子内氨羰基化环化方法，该方法以胺为亲核试剂，草酸作为原位CO替代物，从2-碘苯基碳二亚胺合成具有潜在生物活性的2-（烷基氨基/氨基）-3-芳基喹唑啉-4（3H）-酮类似物。使用了各种环状/非环状伯胺和仲胺，以良好至优异的产率选择性地生成了取代的2-（烷基氨基）-3-芳基喹唑啉-4（3H）-酮。此外，我们扩展了所开发的策略，分别固定两个氨基甲酸铵和草酸作为气态NH和CO源，用于合成2-氨基-3-芳基喹唑啉-4（3H）-酮衍生物。此外，Pd@PS催化剂的克级适用性、多样的底物范围和高可回收性是所开发方案的主要成果。
