TY - JOUR
T1 - The reactivity of Oxone towards 4,6-di(cycloamino)-1,3-phenylenediamines
T2 - synthesis of spirocyclic oxetane ring-fused imidazobenzimidazoles
AU - Al-Dabbagh, Fawaz
AU - Conboy, Darren
PY - 2020
Y1 - 2020
N2 - Spirocyclic oxetane ring-fused imidazo[4,5-f]benzimidazole and imidazo[5,4-f]benzimidazole are reported. Oxone-mediated ring-closures to give imidazobenzimidazoles require acid and the functionalization of the 4,6-di(cycloamino)-1,3-phenylenediamine to the anilides. This is in contrast to benzimidazole forming oxidative cyclizations, which use 2-(cycloamino)anilines and require no acid. New evidence for N-oxide and nitroso-intermediates in respective imidazobenzimidazole and benzimidazole forming reactions is provided.
AB - Spirocyclic oxetane ring-fused imidazo[4,5-f]benzimidazole and imidazo[5,4-f]benzimidazole are reported. Oxone-mediated ring-closures to give imidazobenzimidazoles require acid and the functionalization of the 4,6-di(cycloamino)-1,3-phenylenediamine to the anilides. This is in contrast to benzimidazole forming oxidative cyclizations, which use 2-(cycloamino)anilines and require no acid. New evidence for N-oxide and nitroso-intermediates in respective imidazobenzimidazole and benzimidazole forming reactions is provided.
KW - Chemistry
U2 - 10.24820/ark.5550190.p011.229
DO - 10.24820/ark.5550190.p011.229
M3 - Article
SN - 1551-7004
VL - 2020
SP - 180
EP - 191
JO - Arkivoc
JF - Arkivoc
IS - vii
ER -