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no1uno
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Here is something that might be of interest - Dr Dakin (funnily enough) found that by oxidising (Strecker deg) amino acids (http://www.biochemj.org/bj/010/0319/0100319.pdf), including histamine, the corresponding nitrile/aldehyde was formed in good yield. In this case
the imidazole-4-acetonitrile. Wonder if that could be hydrolysed to imidazole-4-acetamide and if so, could we hit that with more hypochlorite to get
imidazole-4-methylamine? Because if that worked, then deaminative-hydrolysis of the methylamine would give the imidazole-4-aldehyde? Oxidation of
which would leave us with a cheap and nasty route to imidazole via decarboxylation (ala orgsyn: http://www.orgsynth.org/orgsyn/pdfs/CV3P0471.pdf). Yeah, it is multistep, but I can't think of a one-pot that has a chance.
Notice also the use of the same oxidant to form HCN & Formaldehyde from glycine, and acetonitrile & acetaldehyde from alanine.
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Globey
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It's nice when old threads get updated...you get to see stuff you might never have found otherwise. Think I saw a journal article where they were
oxidizing phenylalanine to the nitrile electrically with Br-. It was very simple and had 1-2 steps if memory serves me.
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