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Topic: Phosphoryloxy-ifying reagents  (Read 3417 times)

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Offline limpet chicken

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Phosphoryloxy-ifying reagents
« on: November 29, 2004, 08:02:14 PM »
I am looking into an organic synthesis at the moment, and am a little confused, what reagents are suitable for adding a phosphoryloxy group onto an indole ring?

I looked for comments relating to synthesis of psilocin or psilocybin, these are NOT the compounds I am trying to synthesize, it just so happened that they have a 4-phosphoryloxy group on the indole ring.

What reagents would do this, and in various positions, the alpha and beta positions of the secondary amine are of little importance, but I would still be interested, I am mainly looking into phosphoryloxylating positions on the indole ring itself.

I though of perhaps phosphorus oxychloride, would that work? also, there is a secondary amine group present on the molecule, would phosphorus oxychloride attack a secondary amine, or are protection/deprotection needed, or perhaps add the secondary amine group after phosphorylating step is complete, or even, would phosphorus oxychloride perform a nucleophillic chlorination instead of introducing the phosphoryloxy group on the indole ring?

What about phosphoryloxylations (don't think the term is correct, but it is closes I can get) in general on indole compounds, and for that matter, secondary amine introductions, even on the heterocyclic nitrogen?

Thanks once again people :)
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