TY - JOUR
T1 - Incorporating morpholine and oxetane into benzimidazolequinone anti-tumor agents
T2 - the discovery of 1,4,6,9-tetramethoxyphenazine from hydrogen peroxide and hydroiodic acid-mediated oxidative cyclizations
AU - Conboy, Darren
AU - Mirallai, Styliana I.
AU - Craig, Austin
AU - McArdle, Patrick
AU - Al-Kinani, Ali A.
AU - Barton, Stephen
AU - Aldabbagh, Fawaz
N1 - Note: This work was supported by Kingston University and the Irish Research Council.
PY - 2019/8/2
Y1 - 2019/8/2
N2 - The reactivity of hydrogen peroxide and catalytic hydroiodic acid towards 3,6-dimethoxy-2-(cycloamino)anilines is tunable to give ring-fused benzimidazoles or 1,4,6,9-tetramethoxyphenazine in high yield. Mechanisms via a detected nitroso-intermediate are proposed for oxidative cyclization and the unexpected intermolecular displacement of the oxazine. An aqueous solution of molecular iodine is capable of the same transformations. Oxidative demethylation gave targeted benzimidazolequinones, including without cleavage of the incorporated oxetane.
AB - The reactivity of hydrogen peroxide and catalytic hydroiodic acid towards 3,6-dimethoxy-2-(cycloamino)anilines is tunable to give ring-fused benzimidazoles or 1,4,6,9-tetramethoxyphenazine in high yield. Mechanisms via a detected nitroso-intermediate are proposed for oxidative cyclization and the unexpected intermolecular displacement of the oxazine. An aqueous solution of molecular iodine is capable of the same transformations. Oxidative demethylation gave targeted benzimidazolequinones, including without cleavage of the incorporated oxetane.
KW - Chemistry
U2 - 10.1021/acs.joc.9b01427
DO - 10.1021/acs.joc.9b01427
M3 - Article
SN - 0022-3263
VL - 84
SP - 9811
EP - 9818
JO - The Journal of Organic Chemistry
JF - The Journal of Organic Chemistry
IS - 15
ER -