Three-component, one-pot sequential synthesis of N-aryl, N'-alkyl barbiturates.
[reaction: see text] Condensation between N-alkyl, N'-aryl carbodiimides and malonic acid monoesters leads to a high-yield formation of N-acyl urea derivatives that could be cyclized to C-monosubstituted barbiturates by addition of a suitable base in a one-pot sequential fashion. In the presence of an electrophile, the last step gives rise to a one-pot, three-component sequential synthesis of fully substituted barbiturates.
Volonterio
Alessandro
A
Dipartimento di Chimica, Materiali ed Ingegneria Chimica G. Natta del Politecnico di Milano, C.N.R-Istituto di Chimica del Riconoscimento Molecolare, Sezione A. Quilico, via Mancinelli 7, I-20131 Milano, Italy. alessandro.volonterio@polmi.it
Zanda
Matteo
M
D000478:Alkylation; D001463:Barbiturates / Q000138:chemical synthesis / Q000737:chemistry*; D004146:Dioxanes / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D008314:Malonates / Q000737:chemistry; D015394:Molecular Structure; D012972:Sodium Hydroxide / Q000737:chemistry
D001463:Barbiturates; D004146:Dioxanes; D004952:Esters; D008314:Malonates; D012972:Sodium Hydroxide; C030290:malonic acid; C025223:1,4-dioxane