Synthesis of imidazolidin-2-one-4-carboxylate and of (tetrahydro)pyrimidin-2-one-5-carboxylate via an efficient modification of the Hofmann rearrangement.
A mild and efficient methodology for the rearrangement of protected asparagine and protected glutamine is reported; good results are obtained with a wide selection of protecting groups.
Angelici
Gaetano
G
Dipartimento di Chimica G. Ciamician-Alma Mater Studiorum, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy.
Contaldi
Simone
S
Green
Sarah Lynn
SL
Tomasini
Claudia
C
D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D048289:Imidazolidines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry
C530350:(tetrahydro)pyrimidin-2-one-5-carboxylate; D001565:Benzoates; D002264:Carboxylic Acids; D048289:Imidazolidines; D011744:Pyrimidinones; C530351:imidazolidin-2-one-4-carboxylate