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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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Publication details

The article was received on 12 Sep 2018, accepted on 18 Oct 2018 and first published on 18 Oct 2018


Article type: Edge Article
DOI: 10.1039/C8SC04061C
Chem. Sci., 2019,10, 569-575
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    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

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

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