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NIS/PhI(OAc) 2 ‐Mediated Diamination/Oxidation of N ‐Alkenyl Formamidines: Facile Synthesis of Fused Tricyclic Ureas
Author(s) -
Zhang Jun,
Wu Weijie,
Zhang Xuejun,
Zhang Gengtao,
Xu Sheng,
Shi Min
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201403281
Subject(s) - tricyclic , succinimide , chemistry , bicyclic molecule , medicinal chemistry , combinatorial chemistry , alkyl , oxidation process , organic chemistry , pulp and paper industry , engineering
Facile synthesis of bicyclic ureas by NIS/PhI(OAc) 2 ‐mediated diamination/oxidation of N‐alkenyl formamidines is reported. Bulky aromatic groups such as 2,6‐diisopropylphenyl and mesityl and alkyl groups were tolerated towards the process. Several control experiments have been performed, and the reaction outcomes indicate that the oxidation process is probably concerted with the diamination cyclization, and succinimide generated from NIS‐mediated aminoamidiniumation step promoted the PhI(OAc) 2 ‐mediated oxidation step. The new methodology provides an efficient method for the synthesis of fused tricyclic ureas.