title: Synthesis of 2-amino-4-pyrimidinones from resin-bound guanidines prepared using bis(allyloxycarbonyl)-protected triflylguanidine.
abstract: We have synthesized novel heterocyclic compounds from resin-bound guanidines. For this purpose, an amine immobilized on a solid support was acylated with protected amino acids. Following the deprotection, the liberated amines were guanidinylated utilizing a new member of the family of diurethane-protected triflyl guanidine reagents, N,N'-bis(allyloxycarbonyl)-N' '-triflylguanidine. The deprotected guanidines were subsequently regioselectively cyclized with beta-keto esters yielding novel compounds containing heterocyclic structures in high purities.
authors.affiliation: Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, California 92093-0343, USA.
authors.forename: Christoph W
authors.initials: CW
authors.lastname: Zapf
authors.forename: Murray
authors.initials: M
authors.lastname: Goodman
mesh_terms: D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D006146:Guanidines / Q000737:chemistry*; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry; D012117:Resins, Synthetic / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000588:Amines; D000596:Amino Acids; D004952:Esters; D006146:Guanidines; D011744:Pyrimidinones; D012117:Resins, Synthetic; D012997:Solvents