A divergent synthetic pathway for pyrimidine-embedded medium-sized azacycles through an N-quaternizing strategy. Issue 2 (24th October 2018)

• Record Type: Journal Article
• Authors: Choi, Yoona; Kim, Heejun; Park, Seung Bum
• Is Part Of: Chemical science. Volume 10:Issue 2(2019)
• Page Start: 569
• Page End: 575
• Publication Date: 2018-10-24
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c8sc04061c
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A new divergent synthetic pathway for skeletally distinct pyrimidine-containing medium-sized azacycles was developed. Diversity-generating reactions via selective bond cleavages or migrations from N-quaternized intermediates were designed, and 14 discrete core skeletons were synthesized in an efficient manner. The skeletal diversity of the resulting molecular frameworks was confirmed by chemoinformatic analysis. 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.