H3PW12O40@nano‐ZnO: An efficient, recyclable, and eco‐friendly catalyst for the green synthesis of novel benzo[a]pyrimido[5′, 4′:5, 6]pyrano[2, 3‐c]phenazines via sequential multicomponent reactions under microwave irradiation. Issue 8 (1st May 2018)

• Record Type: Journal Article
• Authors: Mohammadrezaei, Maryam; Mohebat, Razieh; Tabatabaee, Masoumeh
• Is Part Of: Journal of the Chinese Chemical Society. Volume 65:Issue 8(2018)
• Page Start: 1007
• Page End: 1013
• Publication Date: 2018-05-01
• Subjects: benzophenazine -- environmentally friendly -- H3PW12O40@nano‐ZnO -- microwave irradiation -- multicomponent reactions (MCRs) -- pyran derivative; Chemistry -- Periodicals; Electronic journals; 540.5
• DOI: 10.1002/jccs.201700359
• Languages: English
• ISSNs: 0009-4536

Abstract

Abstract : A simple and efficient single‐pot synthesis of novel heteroaryl‐substititued benzo[ a ]pyrimido[5′, 4′:5, 6]pyrano[2, 3‐ c ]phenazines has been developed via initial Knoevenagel, subsequent Michael, and final heterocyclization reactions of 2‐hydroxynaphthalene‐1, 4‐dione, o ‐phenylenediamine, aromatic aldehydes, and barbituric acid in the presence of H3 PW12 O40 @nano‐ZnO as a recyclable heterogeneous catalyst in EtOH under microwave irradiation (MWI). This sequential green process with several advantages, such as operational simplicity, high yields, low cost, easy handling, eco‐friendliness and reusability of the catalyst, absence of any tedious work‐up or purification, and avoidance of hazardous or toxic reagents/catalysts/solvents, opens an effective and convenient way to pyrano‐functionalized benzophenazine systems, which are promising compounds for different biomedical applications. Abstract : A simple, efficient, single‐pot synthesis of novel heteroaryl‐substituted benzo[ a ]pyrimido[5′, 4′:5, 6]pyrano[2, 3‐ c ]phenazines has been developed via initial Knoevenagel, subsequent Michael, and final heterocyclization reactions of 2‐hydroxynaphthalene‐1, 4‐dione, o ‐phenylenediamine, aromatic aldehydes, and barbituric acid in the presence of H3 PW12 O40 @nano‐ZnO as a recyclable heterogeneous catalyst in EtOH under microwave irradiation (MWI). This sequential green process with several advantages, such as operational simplicity, high yield, low cost, easy handling, eco‐friendliness and reusability of the catalyst, absence of any tedious work‐up or purification, and avoidance of hazardous or toxic reagents/catalysts/solvents, opens an effective and convenient way to pyrano‐functionalized benzophenazine systems, which are promising compounds for different biomedical applications.