What is the mechanisms of this reaction? How feasible is this reaction? Can it happen under relatively mild conditions if it is intermolecular?
Answer
A reasonable mechanism for the transformation is shown below. Since this is under basic conditions, I've written a mechanism that avoids cationic intermediates. Deprotonating the hydrazine gives a very nucleophilic nitrogen that can attack the nitro group. Proton transfer gives a nitrogen anion, which can kick out hydroxide. Two additional proton transfer steps lead to the product, HOBt.
A SciFinder search didn't reveal any examples of the intermolecular variant of this reaction, although I didn't find this exact intramolecular reaction either.
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