title: Study of the Reactivities of Acid-Catalyzed O-Benzylating Reagents Based on Structural Isomers of 1,3,5-Triazine.
abstract: We have demonstrated O-benzylating abilities of both 4,6-bis(benzyloxy)-1,3,5-triazin-2(1H)-one (DiBOT) and 6-(benzyloxy)-1,3,5-triazine-2,4(1H,3H)-dione (MonoBOT), which have been previously suggested as reaction intermediates of the acid-catalyzed benzylation of 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT). We studied the effect on the reactivity of acid-catalyzed O-benzylation caused by the isomeric core triazine structures in these compounds by carrying out a kinetic study and estimating relative basicities using model compounds. Since MonoBOT showed superior reactivity, 1,3,5-triazine-2,4(1H,3H)-dione is a promising core structure for acid-catalyzed alkylating reagents.
authors.affiliation: Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University , Kakuma-machi, Kanazawa 920-1192, Japan.
authors.forename: Hikaru
authors.initials: H
authors.lastname: Fujita
authors.affiliation: Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University , Kakuma-machi, Kanazawa 920-1192, Japan.
authors.forename: Naoko
authors.initials: N
authors.lastname: Hayakawa
authors.affiliation: Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University , Kakuma-machi, Kanazawa 920-1192, Japan.
authors.forename: Munetaka
authors.initials: M
authors.lastname: Kunishima