Aminolysis of an N-Diazeniumdiolated Amidine as an Approach to Diazeniumdiolated Ammonia
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Aminolysis of an N-Diazeniumdiolated Amidine as an Approach to Diazeniumdiolated Ammonia
Recent theoretical studies have suggested that the parent diazeniumdiolate ion, H2N-N(O)═NO(-) ("diazeniumdiolated ammonia"), might be stable enough to be isolated and that it could potentially serve as a uniquely advantageous prodrug form of bioactive nitroxyl (HNO). Here, we report on an attempt to isolate its O(2)-benzylated derivative by aminolysis of the C═N bond in PhC(NH2)═N-N(O)═NOBn. T...
متن کاملNitrogen-bound diazeniumdiolated amidines.
In contrast to amidines bearing ionizable alpha-CH bonds, which react with nitric oxide (NO) to add diazeniumdiolate groups at their alpha-carbons, benzamidine forms an N-bound diazeniumdiolate that can be further derivatized at the other amidine nitrogen and/or the terminal oxygen to form caged NO compounds as potential NO prodrugs.
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Nitrous oxide as a primary product in base-mediated β-elimination reactions of diazeniumdiolated benzylamine derivatives.
We report an unexpected β-elimination pathway by which diazeniumdiolated benzylamines of structure Bn-N(R)-N(O)=N-OR' undergo base-mediated fragmentation to generate N(2)O as the only gaseous product. The reaction is especially rapid for R = 2-hydroxyethyl, in which the hydroxyl group anchimerically assists benzylic proton removal with concomitant expulsion of PhCH=NR and R'OH.
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2014
ISSN: 0022-3263,1520-6904
DOI: 10.1021/jo500551n