Issue 2, 2019

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
12 set 2018
Accepted
18 out 2018
First published
18 out 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 569-575

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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