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Topic: Question of Mechanism  (Read 2400 times)

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Offline Super Newb

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Question of Mechanism
« on: September 09, 2012, 07:24:06 AM »
Hi all! I was browsing through some thesis and I am wondering what could be a possible mechanism for the synthesis of 42 to 43. Any help will be appreciated :)
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Offline Dan

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Re: Question of Mechanism
« Reply #1 on: September 09, 2012, 11:36:07 AM »
Identify electrophiles, nucleophiles and acidic protons. Think about how the reagents can interact.

Hint: Consider the mechanism of the aldol condensation, this one is very similar.
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Offline Super Newb

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Re: Question of Mechanism
« Reply #2 on: September 09, 2012, 12:40:16 PM »
Quote from: Dan on September 09, 2012, 11:36:07 AM
Identify electrophiles, nucleophiles and acidic protons. Think about how the reagents can interact.

Hint: Consider the mechanism of the aldol condensation, this one is very similar.

I have attached my proposed mechanism, I don't think that I am anywhere close to the actual mechanism.

Firstly, I suspect that the 2-methyl of the indoline has an acidic hydrogen (but I do not have the actual reason) and the rest is shown below  :)
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Offline orgopete

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Re: Question of Mechanism
« Reply #3 on: September 09, 2012, 10:29:12 PM »
You have satisfactorily connected the groups in a rational manner. I might be a little more particular with the anilide anion in the first condensation product. There are a number of protonation reactions. It would be difficult to determine their exact order of occurrence.
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