Mono C-alkylation and mono C-benzylation of barbituric acids through zinc/acid reduction of acyl, benzylidene, and alkylidene barbiturate intermediates
Through systematic exploration of reaction conditions, very efficient preparative procedures for obtaining large quantities of substituted 5-alkyl and 5-benzylbarbituric acids were developed. The procedure involves a two step preparation in which the second step is zinc dust/acid reduction. For preparation of 5-alkylbarbiturates, the first step is the preparation of either 5-acyl or 5-alkylidenebarbiturate. If 5-benzylbarbiturate is the target product, then the first step includes the preparation of 5-benzylidene. Regardless of the nature of the first step, all reactions presented synthetic yields around 90% and isolation and purification involves only crystallization.
Jursic, Branko S.,Stevens, Edwin D.
p. 2203 - 2210
(2007/10/03)
Reductive C-alkylation of barbituric acid derivatives with carbonyl compounds in the presence of platinum and palladium catalysts
Effective synthetic procedures for the preparation of mono- and di-C-alkylated barbituric acid derivatives through palladium and platinum catalytic hydrogenation of solutions of barbituric acids (unsubstituted, N-mono, and N,N′-disubstituted barbituric acids) and carbonyl compounds (aliphatic and aromatic aldehydes and ketones).
Jursic, Branko S.,Neumann, Donna M.
p. 4103 - 4107
(2007/10/03)
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