14716-41-7Relevant academic research and scientific papers
o-Nitrobenzyl as a photocleavable nitrogen protecting group for indoles, benzimidazole, and 6-chlorouracil
Voelker, Troy,Ewell, Tim,Joo, Jean,Edstrom, Eric D.
, p. 359 - 362 (1998)
The potential for the o-nitrobenzyl group as an alternative nitrogen protecting group for various indoles, benzimidazole, and 6-chlorouracil was determined. Treatment of the appropriate N-H containing substrate with LiH or NaH in DMF followed by o-nitrobenzyl bromide afforded reasonable yields of N-alkylated products. To effect removal of this group, simple photolysis with 300 nm light afforded good yields of starting substrate.
An efficient strategy for N-alkylation of benzimidazoles/imidazoles in SDS-aqueous basic medium and N-alkylation induced ring opening of benzimidazoles
Chakraborty, Ankita,Debnath, Sudipto,Ghosh, Tanmoy,Maiti, Dilip K.,Majumdar, Swapan
, p. 5932 - 5941 (2018/09/18)
A sustainable route for the N-1 alkylation of imidazole and benzimidazole derivatives has been developed under volatile organic solvent free condition in alkaline water-SDS system. Incorporation of SDS in the reaction medium enhances the reaction rate by suppressing the solubility issue that arises for different substrates. This method provides high yield of the alkylated product in a shorter reaction time. For reactive alkyl halides reaction proceeds at ambient temperature whereas in the cases of less reactive alkyl halides require 55–60 °C to complete alkylation process. N-alkylation induced ring opening of the heterocyclic ring in benzimidazole derivatives to multifunctional aromatic compounds were noticed at 60 °C when more than two equivalents of alkyl halide was used.
