Ureas as a New Nucleophilic Reagents for S_NAr Amination and Carbamoyl Amination Reactions in 1,3,7‐Triazapyrene Series

Abstract

The ability of urea anions to react as nucleophiles with alkoxy derivatives of 1,3,7‐triazapyrenes has been investigated. It was found that against all expectations, the products of the substitution of an alkoxy groups (SNipso) by amino group were isolated in good yields. The reactions proceed in anhydrous dimethyl sulfoxide solution at room temperature. But when anions of the mono‐substituted ureas containing bulky substituents were used, the first products of the earlier unknown SNAr reactions of alkyl carbamoyl amination were obtained.

1,3,7-Triazapyrene-Basedortho-Carborane Fluorophores: Convenient Synthesis, Theoretical Studies, and Aggregation-Induced Emission Properties

“…The reaction of 1,3,7-triazapyrene ( 3 ) with electron-rich arenes in concentrated hydrochloric acid yields a limited amount of 6-aryl-1,3,7-triazapyrenes (Scheme , route B) . Oxidative nucleophilic alkoxylation (Scheme , route C) and (alkyl)­amination (Scheme , routes D (S N H ) and E have also been examined to deliver C(6)-heterosubstituted 1,3,7-triazapyrenes. Interestingly, only the C(6)-regioisomer has been obtained for those examples.…”