First practical synthesis of formamidine ureas and derivatives.
Isonitriles and ureas undergo a condensation reaction in the presence of acid chlorides to give formamidine ureas, for which no general synthetic routes currently exist. A mechanism is proposed in which the key intermediate is an electrophilic adduct of isonitrile and acid chloride. The process is tolerant of moderate variability in the nature of the components, and access to formamidine ureas of varying substitution patterns is further enhanced by a facile exchange reaction with amines. [reaction: see text]
Ripka
Amy S
AS
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, USA.
Díaz
David D
DD
Sharpless
K Barry
KB
Finn
M G
MG
D000578:Amidines / Q000138:chemical synthesis*; D000588:Amines / Q000737:chemistry; D008958:Models, Molecular; D009570:Nitriles / Q000737:chemistry; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D000578:Amidines; D000588:Amines; D009570:Nitriles; C077922:formamidine; D014508:Urea