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Synthesis 2012; 44(12): 1907-1914
DOI: 10.1055/s-0031-1290974
DOI: 10.1055/s-0031-1290974
paper
3,5,5-Trisubstituted Hydantoins from Activated (Benzyloxycarbonylamino)malonic Acids
Further Information
Publication History
Received: 21 November 2011
Accepted after revision: 20 March 2012
Publication Date:
09 May 2012 (online)
Abstract
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.
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For recent examples, see:
For the formation of 2-alkoxyoxazol-5(4H)-ones through activation of N-protected amino acids, see, for example:
For the hydantoin cyclization of (alkoxycarbonyl-amino)carboxamides, see, for example:
For the formation of NCAs from 5(4H)-oxazolones, derived from carbamate-protected amino acids, see: