Synthesis of N tau-arylhistidine derivatives via direct N-arylation.
N(tau)-Aryl-histidine derivatives were synthesized using a modified one-step Cu-catalyzed coupling of aryl halides and N-acetylhistidine methyl ester. The latter is much less reactive than imidazole toward aryl halides. p-Chloroiodobenzene coupled with iodine displacement only, whereas m- and p-bromoiodobenzene both gave mixtures of bromo- and iodophenyl products.
Yue
Weimin
W
Department of Medicinal Chemistry, University of Kansas, Lawrence, KS 66045-7582, USA.
Lewis
Stefanie I
SI
Koen
Yakov M
YM
Hanzlik
Robert P
RP
D000818:Animals; D004305:Dose-Response Relationship, Drug; D006639:Histidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D011817:Rabbits; D051381:Rats
D006639:Histidine