Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

A New Synthesis of 4,5,6,7-Tetrahydropyrazolo[1,5-c]pyrimidines by a Retro-Mannich Cascade Rearrangement

Raffaele Colombo A , Kyu Ok Jeon A , Donna M. Huryn B , Matthew G. LaPorte A and Peter Wipf A B C
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.

B Department of Pharmaceutical Sciences, University of Pittsburgh, Pittsburgh, PA 15260, USA.

C Corresponding author. Email: pwipf@pitt.edu

Australian Journal of Chemistry 67(3) 420-425 https://doi.org/10.1071/CH13468
Submitted: 6 September 2013  Accepted: 28 September 2013   Published: 28 October 2013

Abstract

We discovered a new retro-Mannich reaction of in situ prepared pyrazolopyridines to give pyrazolopyrimidines that have hitherto been underrepresented in the heterocyclic chemistry literature. The isolation of a linear hydrolysis product supports a mechanistic hypothesis for this rearrangement process. In order to establish a broader access and explore potential biological applications for these medicinal chemistry building blocks, we investigated the scope of the reaction and generated small amine- as well as amide-based libraries through reductive aminations and amide couplings, respectively.


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