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

Autor:	Janina Schmitz, Michael Gütschow, Marie Hruskova, Lukas Hroch, Gregor Schnakenburg
Rok vydání:	2012
Předmět:	chemistry.chemical_classification medicine.drug_class Aryl Carboxylic acid Organic Chemistry Carboxamide Ring (chemistry) Medicinal chemistry Catalysis chemistry.chemical_compound chemistry Oxalyl chloride medicine Saponification
Zdroj:	Synthesis. 44:1907-1914
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0031-1290974
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::682ec685f0872105d75ddd16c2fbb0e0 https://doi.org/10.1055/s-0031-1290974 Zobrazit plný text záznamu