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.
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Abbreviations
- CDCl3 :
-
Deuterated chloroform
- 1H-NMR:
-
Proton nuclear magnetic resonance spectroscopy
- 13C-NMR:
-
Carbon nuclear magnetic resonance spectroscopy
- TLC:
-
Thin-layer chromatography
- IR:
-
Infrared spectroscopy
- FTIR:
-
Fourier transform infrared spectroscopy
- ESI-HRMS:
-
Electrospray ionization-high-resolution mass spectrometry
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Acknowledgments
SG and GK thank UGC and CSIR, New Delhi, India, for the grant of junior research fellowship and senior research fellowship, respectively.
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Gupta, S., Khanna, G. & Khurana, J.M. 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. Environ Chem Lett 14, 559–564 (2016). https://doi.org/10.1007/s10311-016-0570-6
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DOI: https://doi.org/10.1007/s10311-016-0570-6