75400-65-6Relevant academic research and scientific papers
The N-tert-butylcarbamoyl directed metalation group for the regiospecific synthesis of 2-substituted pyrroles and indoles
Gharpure,Stoller,Bellamy,Firnau,Snieckus
, p. 1079 - 1082 (2007/10/02)
The N-tert-butylcarbamoyl serves as a useful, readily removable (LiOH/MeOH/THF) new directed metalation group for the synthesis of 2-substituted pyrroles and indoles.
Synthesis and Reactions of N-Protected 2-Lithiated Pyrroles and Indoles. The tert-Butoxycarbonyl Substituent as a Protecting Group
Hasan, Iltifat,Marinelli, Edmund R.,Lin, Li-Ching Chang,Fowler, Frank W.,Levy, Alan B.
, p. 157 - 164 (2007/10/02)
N-(tert-Butoxycarbonyl)pyrrole and N-(tert-butoxycarbonyl)indole have been prepared and lithiated at the 2-position with lithium 2,2,6,6-tetramethylpiperidide and tert-butyllithium, respectively.These lithium reagents react with a variety of electrophiles to give the 2-substituted N-(tert-butoxycarbonyl)pyrroles and N-(tert-butoxycarbonyl)indoles.The N-(tert-butoxycarbonyl) substituent may be removed rapidly and in high yield from the pyrrole derivatives under basic conditions.For the indole derivatives, the protecting group may be removed with either acidic or basic conditions.
