Issue 40, 2013

Pyrrolo[2,3-d]pyrimidine synthesis through activation of N-benzyl groups by distal amides

Abstract

A new activation mode of CH2–benzylamino groups has been observed during the preparation of pyrrolopyrimidines from Ugi–Smiles adducts of hydroxypyrimidines. The cyclization proceeds via a formal deprotonation of the N-benzyl group followed by trapping of the resulting anion by the alkyne moiety. The key role of the vicinal amide function during the process was pointed out.

Graphical abstract: Pyrrolo[2,3-d]pyrimidine synthesis through activation of N-benzyl groups by distal amides

Supplementary files

Article information

Article type
Communication
Submitted
17 Jul 2013
Accepted
13 Aug 2013
First published
14 Aug 2013

Org. Biomol. Chem., 2013,11, 6883-6885

Pyrrolo[2,3-d]pyrimidine synthesis through activation of N-benzyl groups by distal amides

L. El Kaïm, L. Grimaud and S. Wagschal, Org. Biomol. Chem., 2013, 11, 6883 DOI: 10.1039/C3OB41477A

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