[DDQM][HSO4]/TBHP as a Multifunctional Catalyst for the Metal Free Tandem Oxidative Synthesis of 2-Phenylquinazolin-4(3 H)-ones

Bidyutjyoti Dutta; Nilakshi Dutta; Apurba Dutta; Montu Gogoi; Sanjay Mehra; Arvind Kumar; Kalyanjyoti Deori; Diganta Sarma

doi:10.1021/acs.joc.2c00908

[DDQM][HSO₄]/TBHP as a Multifunctional Catalyst for the Metal Free Tandem Oxidative Synthesis of 2-Phenylquinazolin-4(3 H)-ones

J Org Chem. 2023 Oct 20;88(20):14748-14752. doi: 10.1021/acs.joc.2c00908. Epub 2022 Aug 12.

Authors

Bidyutjyoti Dutta¹, Nilakshi Dutta¹, Apurba Dutta¹, Montu Gogoi¹, Sanjay Mehra², Arvind Kumar², Kalyanjyoti Deori¹, Diganta Sarma¹

Affiliations

¹ Department of Chemistry, Dibrugarh University, Dibrugarh 786004, Assam, India.
² AcSIR, Salt and Marine Chemicals Division, CSIR-Central Salt and Marine Chemicals Research Institute, Bhavnagar 364002, India.

PMID: 35959933
DOI: 10.1021/acs.joc.2c00908

Abstract

A bifunctional ionic liquid (IL) [DDQM][HSO₄] has been designed and explored as a three-way catalyst for the synthesis of 2-phenylquinazolin-4(3H)-ones from anthranilamide and benzyl alcohol in 3.5 min incorporating microwave irradiation. Photochemically the reaction proceeds for 4 h at room temperature and thermally for 8 h at 120 °C. Further IL-assisted metal, solvent, and base free in situ oxidation of benzyl alcohols to aldehydes shows its task specificity. The multifunctionality of the IL was reestablished with the synthesis of two Wnt pathway antagonists.