Another mechanism problem
Well, my previous problem was answered very quickly by Greg over at Carbon Tet who published the solution in a very understabdable way.
Another one for those who love solving mechanism problems:
You will have to determine the structure of the product and propose a plausible mechanism for this wonderful transformation.
Hope that this one will be answered as quickly as the previous one.
I like heterocycles. 2,5-dimethylpyrrole?
Comment by anon — April 14, 2007 @ 9:18 pm
Yesss!
And what about the mechanism?
Comment by Tynchtyk — April 14, 2007 @ 9:23 pm
one molecule hydrazine condenses with two molecules acetone followed by double tautomerization to give the dienamine. sigmatropic rearrangement forms the C6 skeleton with cleavage of the N-N bond. One of the resulting imine/enamines condenses with the other followed by elimination of ammonia to give the pyrazole ring. Man, its a lot harder to explain a mechanism without pictures…
Comment by anon — April 15, 2007 @ 12:31 am
same idea as Fischer indole synthesis
Comment by anon — April 15, 2007 @ 12:32 am
You’re absolutely right, anon!
I’ll post the solution on Monday.
Comment by Tynchtyk — April 15, 2007 @ 9:46 am
[...] written by Tynchtyk [...]
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