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

Jae Bin Lee; Mi Eun Kang; Joohee Kim; Chang Young Lee; Jung Min Kee; Kyungjae Myung; Jang Ung Park; Sung You Hong

doi:10.1039/c7cc05794f

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

Jae Bin Lee, Mi Eun Kang, Joohee Kim, Chang Young Lee, Jung Min Kee, Kyungjae Myung, Jang Ung Park, Sung You Hong

Department of Materials Science and Engineering

Research output: Contribution to journal › Article › peer-review

42 Citations (Scopus)

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.

Original language	English
Pages (from-to)	10394-10397
Number of pages	4
Journal	Chemical Communications
Volume	53
Issue number	75
DOIs	https://doi.org/10.1039/c7cc05794f
Publication status	Published - 2017

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF-2016R1A2B4015497) and the IT R&D program of MOTIE/KEIT (10046306). We are grateful to Prof. R. Tenne for his helpful comments.

Publisher Copyright:
© 2017 The Royal Society of Chemistry.

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Access to Document

10.1039/c7cc05794f

Cite this

@article{83916a8d656a4bd9b070388ab9459bc1,

title = "Direct diversification of unmasked quinazolin-4(3: H)-ones through orthogonal reactivity modulation",

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.",

author = "Lee, {Jae Bin} and Kang, {Mi Eun} and Joohee Kim and Lee, {Chang Young} and Kee, {Jung Min} and Kyungjae Myung and Park, {Jang Ung} and Hong, {Sung You}",

note = "Funding Information: This work was supported by the National Research Foundation of Korea (NRF-2016R1A2B4015497) and the IT R&D program of MOTIE/KEIT (10046306). We are grateful to Prof. R. Tenne for his helpful comments. Publisher Copyright: {\textcopyright} 2017 The Royal Society of Chemistry.",

year = "2017",

doi = "10.1039/c7cc05794f",

language = "English",

volume = "53",

pages = "10394--10397",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "75",

}

TY - JOUR

T1 - Direct diversification of unmasked quinazolin-4(3: H)-ones through orthogonal reactivity modulation

AU - Lee, Jae Bin

AU - Kang, Mi Eun

AU - Kim, Joohee

AU - Lee, Chang Young

AU - Kee, Jung Min

AU - Myung, Kyungjae

AU - Park, Jang Ung

AU - Hong, Sung You

N1 - Funding Information: This work was supported by the National Research Foundation of Korea (NRF-2016R1A2B4015497) and the IT R&D program of MOTIE/KEIT (10046306). We are grateful to Prof. R. Tenne for his helpful comments. Publisher Copyright: © 2017 The Royal Society of Chemistry.

PY - 2017

Y1 - 2017

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85029612981&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85029612981&partnerID=8YFLogxK

U2 - 10.1039/c7cc05794f

DO - 10.1039/c7cc05794f

M3 - Article

C2 - 28876024

AN - SCOPUS:85029612981

SN - 1359-7345

VL - 53

SP - 10394

EP - 10397

JO - Chemical Communications

JF - Chemical Communications

IS - 75

ER -

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

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this