Paal-Knorr Pyrrole Synthesis – Enamine Intermediate

Sn2

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

This shows the tradtional mechanism for forming a pyrrole ring using a 1,4-diketone and ammonia. The hydroxyl groups are removed as water in two separate dehydration steps, forming enamines in two of the intermediates.

A new mechanism, which does not require enamine formation, has been proposed based on a study using Density Functional Theory.

A. R. Katritzky, D. L. Ostercamp and T. I. Yousaf, Tetrahedron, 1987, 43, 5171–5186.

()

How useful was this page?

Click on a star to rate it!

Average rating / 5. Vote count:

No votes so far! Be the first to rate this page.

As you found this page useful...

Follow us on social media!

We are sorry that this page was not useful for you!

Let us improve this page!

Tell us how we can improve this page (in your own language if you prefer)? If you would like a response, please include your email address e.g. [email protected]

Provided by the