o-Nitrobenzyl as a photocleavable nitrogen protecting group for indoles, benzimidazole, and 6-chlorouracil

Article abstract of DOI:10.1016/S0040-4039(97)10600-1

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.