title: One-pot, regiospecific assembly of (E)-benzamidines from δ- and γ-amino acids via an intramolecular aminoquinazolinone rearrangement.
abstract: The efficient generation of novel, N-linked benzamidines resulting from a regiospecific rearrangement of quinazolinones is described. This methodology study explored reaction parameters including the effect of changing solvent and temperature, as well as varying electronic substituents on the structural core. The transformation was extensively optimized in terms of reaction conditions and scope, resulting in a protocol that consistently affords diversely functionalized amidines in high yield. The process permits regional structural derivatization that was previously inaccessible, and the multistep process was also reduced to a telescoped, five-step sequence that efficiently affords pharmacologically unique (E)-benzamidoamidines from N-BOC protected γ- and δ-amino acids.
authors.affiliation: University of Kansas Specialized Chemistry Center, Del Shankel Structural Biology Center, 2034 Becker Drive, Lawrence, KS 66047, USA. jennifer.golden@wisc.edu.
authors.forename: Chad E
authors.initials: CE
authors.lastname: Schroeder
authors.forename: Sarah A
authors.initials: SA
authors.lastname: Neuenswander
authors.forename: Tuanli
authors.initials: T
authors.lastname: Yao
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Aubé
authors.forename: Jennifer E
authors.initials: JE
authors.lastname: Golden
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D001550:Benzamidines / Q000737:chemistry*; D052999:Quinazolinones / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D001550:Benzamidines; D052999:Quinazolinones