Journal of Organic Chemistry p. 2159 - 2165 (1989)
Update date:2022-08-04
Topics: Synthesis Derivatives Lithiation Ortho Regiospecific Phenoxazine
Antonio, Yulia
Barrera, Patricia
Contreras, Olga
Franco, Fidencio
Galeazzi, Edvige
et al.
Under appropriate conditions, phenoxazine bearing a sterically demanding, bulky N-substituent (e.g., α-methylbenzyl or tert-butyldimethylsilyl) undergoes lithiation at C-4 or at C-4 and C-6 with n-butyllithium in THF solution.The lithiated species react with a variety of electrophilic reagents and upon subsequent N-deprotection provide access to 4-mono- or 4,6-disubstituted phenoxazines.This process is of particular synthetic utility (36-54percent yields) when the N-substituent is tert-butyldimethylsilyl.
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