Traceless solid-phase synthesis of 1,2,4-triazoles using a novel amine resin.
[reaction: see text]. A solid-phase route to 5-aryl-3-arylthiomethyl-1,2,4-triazoles has been developed that permits the incorporation of two elements of diversity. The heterocycle was constructed upon a novel 4-benzyloxy-2-methoxybenzylamine (BOMBA) resin, from which traceless cleavage could be effected with dilute TFA. A library of 96 triazoles was produced with an average yield of 26% (84% yield per step) and an average purity of 80%. In a direct comparison, the new BOMBA resin proved to be markedly superior to Rink Amide resin for this application.
Larsen
S D
SD
Combinatorial and Medicinal Chemistry Research, Pharmacia Corporation, Kalamazoo, Michigan 49007, USA. scott.d.larsen@pharmacia.com
DiPaolo
B A
BA
D000588:Amines / Q000737:chemistry; D002626:Chemistry, Pharmaceutical; D020650:Combinatorial Chemistry Techniques; D012117:Resins, Synthetic / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis*
D000588:Amines; D012117:Resins, Synthetic; D014230:Triazoles; C045575:1,2,4-triazole