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Chem Commun (Camb). 2017 Sep 19;53(75):10394-10397. doi: 10.1039/c7cc05794f.

Direct diversification of unmasked quinazolin-4(3H)-ones through orthogonal reactivity modulation.

Author information

1
School of Energy and Chemical Engineering, Ulsan National Institute of Science and Technology (UNIST), 50 UNIST-gil, Ulsan 44919, Republic of Korea. syhong@unist.ac.kr.
2
School of Materials Science and Engineering, UNIST, 50 UNIST-gil, Ulsan 44919, Republic of Korea. jangung@unist.ac.kr.
3
Department of Chemistry, UNIST, 50 UNIST-gil, Ulsan 44919, Republic of Korea.
4
Center for Genomic Integrity (CGI), Institute for Basic Science (IBS), School of Life Science, UNIST, 50 UNIST-gil, Ulsan 44919, Republic of Korea.
5
School of Energy and Chemical Engineering, Ulsan National Institute of Science and Technology (UNIST), 50 UNIST-gil, Ulsan 44919, Republic of Korea. syhong@unist.ac.kr and Center for Genomic Integrity (CGI), Institute for Basic Science (IBS), School of Life Science, UNIST, 50 UNIST-gil, Ulsan 44919, Republic of Korea.

Abstract

Here we report a set of direct functionalization methods of unmasked 2-phenylquinazolin-4(3H)-ones, a privileged alkaloid core, without the installation/removal event of protecting groups or exogenous coordinating moieties. Divergent pathways were modulated with transition-metal catalysts by suppressing competitive reactivities, leading to N-arylation, annulative π-extension, or C-H fluorination.

PMID:
28876024
DOI:
10.1039/c7cc05794f

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