10.1002/ejoc.202000637
European Journal of Organic Chemistry
COMMUNICATION
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further selenates uracil via in situ heterolysis generated RSe+ to
furnish the target product and release one proton. Finally, proton is
reduced to H2 at the surface of cathode to complete this conversion.
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In summary, we have developed an eco-friendly and efficient
electrochemical selenylation of uracils for the synthesis of 5-
selenouracil derivatives. This reaction was performed in the air
condition, easy operation, transition metal catalyst free and
additional oxidants free to provid a rapid and practical protocol to
5-selenouracil derivatives. And further studies on the applications
of 5-selenouracil in drug design are currently ongoing in our
laboratory.
[4]
Experimental Section
Uracil 1 (0.2 mmol), diselenide 2 (0.1 mmol), NH4I (0.02 mmol)
were placed in a 10 mL three-necked round-bottomed flask.The
flask was equipped with a condenser, a C plate (1 cm x 1 cm)
anode and a platinum plate (1 cm x 1 cm) cathode. DMF (8.0 mL)
were added. The electrolysis was carried out under air atmosphere
at 50 oC using a constant current of 3 mA until complete
consumption of the substrate (monitored by TLC, about 2 h). The
mixture was cooled and diluted with brine, and the product was
extracted with ethyl acetate (3 × 10 mL). The organic layer was
dried over anhydrous Na2SO4 and concentrated under reduced
pressure. The residue was chromatographed through silica gel
eluting with ethyl acetate/petroleum ether to give the desired
products .
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We would like to thank the National Natural Science Foundation of
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(2018GXNSFBA138050,
2018GXNSFAA138165
and
2019GXNSFAA245035), and Guangxi Science and Technology
Base and Talents Program (AD18281035, AD18281028) for
financial support.
.
.
Keywords: Electrochemical
Selenylation
5-Selenouracil
derivatives
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