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Topic: Knorr Pyrrole Synthesis  (Read 13149 times)

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Offline Skullmonkee

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Knorr Pyrrole Synthesis
« on: September 02, 2007, 02:59:32 AM »
Hey, i was wondering if anyone can help me with the mechanism of this synthesis in detail, or if anyone could point me in the direction of any examples or references.

This is different from the Pall-Knorr Pyrolle synthesis also.

Thanks for your help.

Offline Dan

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Re: Knorr Pyrrole Synthesis
« Reply #1 on: September 02, 2007, 09:22:35 AM »
Ta-da!! http://www.unine.ch/chim/ecsoc-2/ECSOC-04.html

This was the 3rd result when I googled "knorr pyrrole synthesis"...

The wikipedia article, which was the 1st result on google, has six literature references that you could look at.
My research: Google Scholar and Researchgate

Offline Skullmonkee

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Re: Knorr Pyrrole Synthesis
« Reply #2 on: September 03, 2007, 07:51:27 AM »
Okay, obviously i would have googled before i posted...  Notice how i said "detailed" ?  Also if you have a look at the wikipedia articles like i did before i posted you would see they are very general indeed.

Thanks for your answer even though you tried to be a smart ass.  Why do you think i would post on a chemistry forum when there are obvious links in google?

Offline Dan

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Re: Knorr Pyrrole Synthesis
« Reply #3 on: September 03, 2007, 09:33:04 AM »
Why do you think i would post on a chemistry forum when there are obvious links in google?

Because people do exactly that on a regular basis, I apologise if I offended, I just misjudged what you were looking for.

The scheme in the link I posted is quite detailed, the numbers below refer to the reaction arrows between the intermediates, and explain what I think is going on with regards to mechanism.

1. Reduction of the oxime (by Zn)
2. Imine formation & tautomerisation to the enamine intermediate shown.
3. Nucleophilic addition of the enamine to the carbonyl (which gives the cyclic imine, tautomerise to the enamine intermediate shown).
4. Dehydration

Hope that helps and makes sense.
My research: Google Scholar and Researchgate

Offline Skullmonkee

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Re: Knorr Pyrrole Synthesis
« Reply #4 on: September 17, 2007, 07:00:50 AM »
Sorry i guess that there are a lot of people who tend to do that.

At least you took the time to try to help, so thanks.  Documented studies are harder than i thought to find .


Offline titan517

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Re: Knorr Pyrrole Synthesis
« Reply #5 on: February 07, 2012, 05:09:19 PM »
Hey I would like to know if there is a detailed mechanism for the scheme in the link posted...Just can't seem to put it together even with the steps you guys posted..

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