A facile eco-friendly approach for the one-pot synthesis of 3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazine-5,10-diones using glycerol as a green media

Abstract

1,3-Oxazines have a wide variety of biological activities. Naphthoquinone scaffolds also exhibit several biological responses such as antithrombotic, apoptosis and lipoxygenase inhibitors. There is, therefore, a need to develop efficient green methodologies for hybridizing the two scaffolds in a single entity. Herein, we report a novel protocol for the synthesis of 3-aryl-3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazine-5,10-diones by one-pot three-component condensation of 2-hydroxy-1,4-naphthoquinone, aromatic amines and formaldehyde in glycerol at 50 °C. After separation of products, the glycerol–water layer was extracted using ethyl acetate and the dried glycerol layer was successfully reused several times. The products were obtained in 85–95 % yields in 5–10 min. This environmentally benign protocol holds advantages of high yields, operational simplicity and easy workup over our earlier report.