3,5,5-Trisubstituted Hydantoins from Activated (Benzyloxycarbonylamino)malonic Acids

作者：Hroch Lukas; Hruskova Marie; Schmitz Janina; Schnakenburg Gregor; Guetschow Michael

来源：Synthesis (Germany), 2012, 44(12): 1907-1914.

DOI：10.1055/s-0031-1290974

• hydantoins
• malonic acids
• oxazolones
• nitrogen heterocycles
• ring closure
• ring opening

Diethyl 2-alkyl-2-(benzyloxycarbonylamino)malonates were saponified, activated with oxalyl chloride, and treated with primary aromatic amines. This gave 3,5-disubstituted hydantoin-5-carboxamides. As second products, 2-alkyl-2-formamido-N-1,N-3-bis(aryl)malonamides were isolated. The formation of both types of products is expected to include a cyclization to 2-alkoxyoxazol-5(4H)-ones, acting as precursor for the hydantoins, or a further transformation to N-carboxy anhydrides, their chloride-promoted ring opening, and subsequent conversion to give the bis(aryl)malonamides.

• 出版日期2012-6