Abstract
The electroreductive intramolecular coupling of barbituric acids with aliphatic ketones gave five- and six-membered cyclized products stereospecifically. When the same reactions were carried out with SmI2, only a five-membered cyclized product was formed as the single stereoisomer different from that obtained by the electroreduction. The cyclized products were stereospecifically transformed to the corresponding deoxygenated compounds by reduction with Et3SiH–BF3·Et2O. Similarly, the electroreductive intramolecular coupling of barbituric acids with O-methyl oximes gave five- and six-membered cyclized products. The DFT calculations suggested that the electroreductive intramolecular coupling proceeds through the protonated radical generated by one-electron transfer and subsequent protonation to the barbituric acid moiety.
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