Premium
Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2‐Aryldiamines
Author(s) -
Faggyas Réka J.,
Sloan Nikki L.,
Buijs Ned,
Sutherland Andrew
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900463
Subject(s) - chemistry , reagent , benzotriazole , intramolecular force , combinatorial chemistry , aryl , functional group , nitrite , organic chemistry , alkyl , polymer , nitrate
An operationally simple method has been developed for the preparation of N ‐unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2‐aryldiamines under mild conditions, using a polymer‐supported nitrite reagent and p ‐tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N ‐alkyl, ‐aryl, and ‐acyl ortho ‐aminoanilines leading to the synthesis of N 1 ‐substituted benzotriazoles. The synthetic utility of this one‐pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α‐amino acid analogue.