Tetrahedron Letters p. 359 - 362 (1998)
Update date:2022-08-03
Topics:
Voelker, Troy
Ewell, Tim
Joo, Jean
Edstrom, Eric D.
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.
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