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The question I have is what is wrong with the proposed mechanism by Kappe and wh

ID: 823545 • Letter: T

Question



The question I have is what is wrong with the proposed mechanism by Kappe and what is the actual mechanism for the Bignelli reaction. Link to noncompress picture: http://gyazo.com/c8a8decf72fe98ed579838c46f589543

This mechanism is superseded by one by Kappe in 1997: This scheme begins with rate determining nucleophilic addition by the urea to the aldehyde [14] [15]. The ensuing condensation step is catalyzed by the addition of acid, resulting in the imine nitrogen. The beta-ketoester then adds to the imine bond and consequently the ring is closed by the nucleophilic attack by the amine onto the carbonyl group. This final step ensues a second condensation and results in the Biginelli compound, taken by Kasliwal.

Explanation / Answer

Bignelli reaction is acid-catalyzed, three-component reaction between an aldehyde, a

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