A nitromethane extrusion reaction for the synthesis of polycyclic benzimidazoheterocycles
Pin-Hui Lin1, Kesavan Stalindurai2, Si-Yuan Chen2
1Graduate Program for Biomedical & Materials Science, Tunghai University, No. 1727, Sec. 4, Taiwan Boulevard, Xitun District, Taichung 40704, Taiwan. yang@thu.edu.tw.
Abstract:
A facile base-promoted annulation of diamines with 4-chloro-3-nitrocoumarins or 4-chloro-3-nitroquinolin-2(1H)-ones affording 6H-benzimidazo[1,2-c][1,3]benzoxazin-6-ones or benzo[4,5]imidazo[1,2-c]quinazolin-6(5H)-ones in moderate to good yields is reported. These metal- and triphosgene-free reactions presumably proceed by the conjugate addition of diamines to 4-chloro-3-nitrocoumarins/4-chloro-3-nitroquinolin-2(1H)-ones, followed by intramolecular cyclization via extrusion of nitromethane and hydrogen chloride to form the target compounds.
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