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N-Methylamino Pyrimidyl Amides (MAPA): Highly Reactive, Electronically-Activated Amides in Catalytic N-C(O) Cleavage

Guangrong Meng1, Roger Lalancette1, Roman Szostak2

  • 1Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.

Organic Letters
|August 23, 2017
PubMed

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
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Acid-catalyzed hydrolysis:
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