Chemoselective Alkylation for Diversity-Oriented Synthesis
of 1,3,4-Benzotriazepin-2-ones and Pyrrolo[1,2][1,3,4]benzotriazepin-6-ones,
Potential Turn Surrogates
posted on 2015-12-18, 00:00authored byAntoine Douchez, William D. Lubell
1,3,4-Benzotriazepin-2-ones
garner interest for medicinal applications,
in part due to their relationship with benzodiazepinones. Ten 1,3,4-benzotriazepin-2-ones 6 and 19 and six pyrrolo[1,2][1,3,4]benzotriazepin-6-ones 7 and 23 were prepared in four to seven steps
and 4–60% overall yields by a divergent strategy from methyl
anthranilate employing chemoselective alkylations of common linear
and cyclic precursors to diversify three triazepinone ring positions
(N1, N3, and C5). X-ray crystallography demonstrated that benzotriazepinone 19g may serve as a γ-turn mimic.