Site‐Selective C–H Amidation of 2‐Aryl Quinazolinones Using Nitrene Surrogates

Kim, Saegun; Jeoung, Daeun; Kim, Kunyoung; Lee, Seok Beom; Lee, Suk Hun; Park, Min Seo; Ghosh, Prithwish; Mishra, Neeraj Kumar; Hong, Suckchang; Kim, In Su

doi:10.1002/ejoc.202001128

Cited by 8 publications

(5 citation statements)

References 45 publications

(28 reference statements)

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“…Sealed tubes (13 × 100 mm 2 ) were purchased from Fischer Scientific and dried in an oven overnight and cooled at room temperature prior to use. 2-Aryl-quinazolin-4(3 H )-ones ( 1a – f , 1h – l , and 1o ) were synthesized according to the literature procedure, and the general procedure and characterization data for the synthesis of unknown 2-aryl-quinazolin-4(3 H )-ones ( 1g , 1m , and 1n ) are reported herein. 5-Methylene-1,3-dioxan-2-one ( 2a ) was prepared according to a literature procedure. , Thin layer chromatography was carried out using plates coated with Kieselgel 60 F 254 (Merck).…”

Section: Methodsmentioning

confidence: 99%

Catalyst-Controlled C–H Allylation and Annulation of 2-Aryl Quinazolinones with 2-Methylidene Cyclic Carbonate

Ko,

Min,

Moon

et al. 2023

J. Org. Chem.

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The site-selective modification of quinazolinone as a privileged bicyclic N-heterocycle is an attractive topic in medicinal chemistry and material science. We herein report the ruthenium(II)catalyzed C−H allylation of 2-aryl quinazolinones with 2-methylidene cyclic carbonate. In addition, tandem C−H allylation and annulation are achieved under rhodium(III) catalysis, resulting in the formation of tetracyclic quinazolinones including a tertiary carbon center. Posttransformations of the synthesized products demonstrate the potential of the developed methodology. A series of mechanistic investigations were also performed.

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Section: Methodsmentioning

confidence: 99%

Catalyst-Controlled C–H Allylation and Annulation of 2-Aryl Quinazolinones with 2-Methylidene Cyclic Carbonate

Ko,

Min,

Moon

et al. 2023

J. Org. Chem.

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“…. 65 The title compound was purified by column chromatography on silica gel with PE/EtOAc (3:1) and obtained as a yellow solid in 45% yield (21.3 mg). 1…”

Section: -(O-tolyl)quinazolin-4(3h)-one (3ag)mentioning

confidence: 99%

Cobalt Homeostatic Catalysis for Coupling of Enaminones and Oxadiazolones to Quinazolinones

Fan

et al. 2023

J. Org. Chem.

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Transition metal catalysis has revolutionized modern synthetic chemistry for its diverse modes of coordination reactivity. However, this versatility in reactivity is also the predominant cause of catalyst deactivation, a persisting issue that can significantly compromise its synthetic value. Homeostatic catalysis, a catalytic process that can sustain its productive catalytic cycle even when chemically disturbed, is proposed herein as an effective tactic to address the challenge. In particular, a cobalt homeostatic catalysis process has been developed for the watertolerant coupling of enaminones and oxadiazolones to quinazolinones. Dynamic covalent bonding serves as a mechanistic handle for the preferred buffering of water onto enaminone and reverse exchange by a released secondary amine, thus securing reversible entry into cobalt's dormant and active states for productive catalysis. Through this homeostatic catalysis mode, a broad structural scope has been achieved for quinazolinones, enabling further elaboration into distinct pharmaceutically active agents.

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“…To date, the selective amination of aliphatic C(sp 3 )–H bonds has mainly been limited to the site-selectivity of unactivated substrates (e.g., tertiary alkyl C–H bonds and benzylic γ-C–H bonds) and activated substrates (e.g., allylic and benzylic C–H bonds)23, [ 25 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 ]. Due to the similar high bond-dissociation energy of aliphatic C-H bonds, only a handful of studies have been conducted to identify the selective amination of aliphatic C(sp 3 )–H bonds.…”

Section: Introductionmentioning

confidence: 99%

Silver Catalyzed Site-Selective C(sp3)−H Bond Amination of Secondary over Primary C(sp3)−H Bonds

et al. 2022

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Sulfamates are widespread in numerous pharmacologically active molecules. In this paper, Silver/Bathophenanthroline catalyzed the intramolecular selective amination of primary C(sp3)−H bonds and secondary C(sp3)−H bonds of sulfamate esters, to produce cyclic sulfamates in good yields and with a high site-selectivity. DFT calculations revealed that the interaction between sulfamates and L10 makes the molecule more firmly attached to the catalyst, benefiting the catalysis reaction. The in vitro anticancer activity of the final products was evaluated in MCF-7 breast cancer cells.

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Site‐Selective C–H Amidation of 2‐Aryl Quinazolinones Using Nitrene Surrogates

Cited by 8 publications

References 45 publications

Catalyst-Controlled C–H Allylation and Annulation of 2-Aryl Quinazolinones with 2-Methylidene Cyclic Carbonate

Catalyst-Controlled C–H Allylation and Annulation of 2-Aryl Quinazolinones with 2-Methylidene Cyclic Carbonate

Cobalt Homeostatic Catalysis for Coupling of Enaminones and Oxadiazolones to Quinazolinones

Silver Catalyzed Site-Selective C(sp3)−H Bond Amination of Secondary over Primary C(sp3)−H Bonds

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