Copper-Mediated N-Arylation of Quinazolinediones

Guy, Collette S.; Jones, T Hugh

doi:10.1055/s-0029-1217724

Cited by 11 publications

(5 citation statements)

References 11 publications

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“…In order to find an efficient synthesis of N (2)-aryl-substituted indazol-3(2 H )-one 3 , the CEL coupling of N (1)-protected indazol-3(2 H )-one 1 with arylboronic acid 2 was investigated based on procedures in the literature to determine optimal conditions [ 23 ]. It appears from the results that the type of solvent did not have a significant effect on the reaction yield ( Table 1 , entries 1–3).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Anti-Inflammatory Activity of N(2)-Arylindazol-3(2H)-One Derivatives: Copper-Promoted Direct N-Arylation via Chan–Evans–Lam Coupling

Kim,

Choi

et al. 2023

Molecules

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Inflammatory-related diseases are becoming increasingly prevalent, leading to a growing focus on the development of anti-inflammatory agents, with a particular emphasis on creating novel structural compounds. In this study, we present a highly efficient synthetic method for direct N-arylation to produce a variety of N(2)-arylindazol-3(2H)-ones 3, which exhibit anti-inflammatory activity. The Chan–Evans–Lam (CEL) coupling of N(1)-benzyl-indazol-3-(2H)-ones 1 with arylboronic acids 2 in the presence of a copper complex provided the corresponding N(2)-arylindazol-3(2H)-ones 3 in good-to-excellent yields, as identified with NMR, MS, and X-ray crystallography techniques. The cell viability and anti-inflammatory effects of the synthesized compounds (3 and 5) were briefly assessed using the MTT method and Griess assay. Among them, compounds 5 exhibited significant anti-inflammatory effects with negligible cell toxicity.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Anti-Inflammatory Activity of N(2)-Arylindazol-3(2H)-One Derivatives: Copper-Promoted Direct N-Arylation via Chan–Evans–Lam Coupling

Kim,

Choi

et al. 2023

Molecules

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“…While transition‐metal (TM) catalyzed C sp 2 −H borylation methodologies are widespread, the catalytic borylation of C sp 3 −H substrates are uniquely challenging because of the sterically demanding geometry of C sp 3 −H compared to planar C sp 2 −H and the absence of easily accessible frontier molecular orbitals for coordination with the catalysts [25] . TM catalyzed methodologies for the C−H functionalization of cyclic amine frameworks have been developed using directing groups, [26–33] such as pyridine as pioneered by the Sawamura group using Rh [28] and Ir [29] complexes (Figure 1a).…”

Section: Introductionmentioning

confidence: 99%

Metal‐Free Directed Site‐Selective Csp³‐H Borylation of Saturated Cyclic Amines

et al. 2023

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The borylation of Csp3‐H bonds is a challenging transformation that is typically restricted to transition metal catalysis. Herein, we report the site‐selective metal‐free Csp3–H borylation of saturated cyclic amines. It is possible to selectively borylate piperidine derivatives at the α or β positions according to the reaction conditions. The mechanism was supported by NMR spectroscopy, calorimetry experiments and density functional theory (DFT) computations. It suggests that the piperidine is dehydrogenated by complexation with BBr3 to produce an enamine intermediate, which is in turn borylated at either the α or β position according to the reaction conditions.

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“…Diboranes with direct boron‐boron single bond are extremely versatile reagents in synthetic chemistry, for example for the catalytic or base‐induced borylation of unsaturated and even saturated substrates [1–5] . These compounds could be three‐ or four‐coordinate at the boron atoms.…”

Section: Introductionmentioning

confidence: 99%

Cationic Symmetrically and Unsymmetrically Substituted Diboranes and Bis(diboranes) with Direct Boron‐Boron Bond: Synthesis by Substitution, Stability and Properties

et al. 2023

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Starting with diboranes with two electron-rich bridging bicyclic guanidinate substituents, we report in this work the rational synthesis of new dicationic symmetrically-and unsymmetrically-substituted diboranes in S N 1-type substitution reactions in which triflato or bromo substituents are replaced by neutral Lewis bases. The scope of such substitution reactions and their rate are analyzed with different pyridine derivatives of variable Lewis basicity. The first substitution step, leading to a mono-cationic diborane with one anionic substituent (triflate or bromide) and one neutral Lewis base, proceeds much faster than the second substitution step leading to a dicationic diborane with two neutral Lewis bases. The different time scales for the substitution steps could be used to conveniently synthesize in one-pot reactions several dicationic, unsymmetrically-substituted diboranes with two different neutral Lewis bases.

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Copper-Mediated N-Arylation of Quinazolinediones

Cited by 11 publications

References 11 publications

Synthesis and Anti-Inflammatory Activity of N(2)-Arylindazol-3(2H)-One Derivatives: Copper-Promoted Direct N-Arylation via Chan–Evans–Lam Coupling

Synthesis and Anti-Inflammatory Activity of N(2)-Arylindazol-3(2H)-One Derivatives: Copper-Promoted Direct N-Arylation via Chan–Evans–Lam Coupling

Metal‐Free Directed Site‐Selective Csp³‐H Borylation of Saturated Cyclic Amines

Cationic Symmetrically and Unsymmetrically Substituted Diboranes and Bis(diboranes) with Direct Boron‐Boron Bond: Synthesis by Substitution, Stability and Properties

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Copper-Mediated N-Arylation of Quinazolinediones

Cited by 11 publications

References 11 publications

Synthesis and Anti-Inflammatory Activity of N(2)-Arylindazol-3(2H)-One Derivatives: Copper-Promoted Direct N-Arylation via Chan–Evans–Lam Coupling

Synthesis and Anti-Inflammatory Activity of N(2)-Arylindazol-3(2H)-One Derivatives: Copper-Promoted Direct N-Arylation via Chan–Evans–Lam Coupling

Metal‐Free Directed Site‐Selective Csp3‐H Borylation of Saturated Cyclic Amines

Cationic Symmetrically and Unsymmetrically Substituted Diboranes and Bis(diboranes) with Direct Boron‐Boron Bond: Synthesis by Substitution, Stability and Properties

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Metal‐Free Directed Site‐Selective Csp³‐H Borylation of Saturated Cyclic Amines