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Issue 2, 2019
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A divergent synthetic pathway for pyrimidine-embedded medium-sized azacycles through an N-quaternizing strategy

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Abstract

Medium-sized heterocycles have recently received significant attention because of their potential roles as modulators of protein–protein interactions, but their molecular diversity and synthetic availability are still inadequate to meet the demand. To address these issues, we developed a new divergent synthetic pathway for skeletally distinct pyrimidine-containing medium-sized azacycles. We introduced N-quaternized pyrimidine-containing polyheterocycles as novel key intermediates for diversity-generating reactions via selective bond cleavages or migrations and prepared 14 discrete core skeletons in an efficient manner. The skeletal diversity of the resulting molecular frameworks was confirmed by chemoinformatic analysis.

Graphical abstract: A divergent synthetic pathway for pyrimidine-embedded medium-sized azacycles through an N-quaternizing strategy

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Supplementary files

Article information


Submitted
12 Sep 2018
Accepted
18 Oct 2018
First published
18 Oct 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 569-575
Article type
Edge Article

A divergent synthetic pathway for pyrimidine-embedded medium-sized azacycles through an N-quaternizing strategy

Y. Choi, H. Kim and S. B. Park, Chem. Sci., 2019, 10, 569
DOI: 10.1039/C8SC04061C

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