Copper-catalyzed one-pot synthesis of 2H-1,4-benzoxazin-3-(4H)-ones from 2-(o-haloaryloxy)acyl chlorides and primary amines

Hu, Qunxian; Xia, Ziming; Zheng, Jie-Ning; Wang, Xiaoxia; Lv, Xin

doi:10.3998/ark.5550190.0013.612

Cited by 4 publications

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“…α-Phenoxyacetic acids of type 6 were prepared from corresponding substituted phenols and α-haloacetic acid following the described procedures (Scheme 1). 28,29 Subsequent activation of acids of type 6, followed by coupling with 2-(2-aminoethyl)benzimidazole (7), led to formation of the target-substituted benzimidazoles 8. Initially, the activation of acids of type 6 was performed using pivaloyl chloride (PivCl), but the reaction of 7 with the mixed anhydrides thus generated was not completely regioselective.…”

Section: ■ Resultsmentioning

confidence: 99%

Synthesis, Biological Evaluation, and Structure–Activity Relationships of Potent Noncovalent and Nonpeptidic Cruzain Inhibitors as Anti-Trypanosoma cruzi Agents

et al. 2014

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The development of cruzain inhibitors has been driven by the urgent need to develop novel and more effective drugs for the treatment of Chagas' disease. Herein, we report the lead optimization of a class of noncovalent cruzain inhibitors, starting from an inhibitor previously cocrystallized with the enzyme (K i = 0.8 μM). With the goal of achieving a better understanding of the structure−activity relationships, we have synthesized and evaluated a series of over 40 analogues, leading to the development of a very promising competitive inhibitor (8r, IC 50 = 200 nM, K i = 82 nM). Investigation of the in vitro trypanocidal activity and preliminary cytotoxicity revealed the potential of the most potent cruzain inhibitors in guiding further medicinal chemistry efforts to develop drug candidates for Chagas' disease.

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Section: ■ Resultsmentioning

confidence: 99%

Synthesis, Biological Evaluation, and Structure–Activity Relationships of Potent Noncovalent and Nonpeptidic Cruzain Inhibitors as Anti-Trypanosoma cruzi Agents

et al. 2014

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Copper‐Catalyzed Amination of Aryl and Alkenyl Electrophiles

2014

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The copper‐catalyzed arylation and vinylation of nitrogen nucleophiles is a highly versatile method for the construction of sp 2 C–N bonds. Copper‐catalyzed C–N bond formation has an extensive history and the field has been reinvigorated with the development of ligand‐promoted catalyst systems that provide general and effective reactions under relatively mild conditions. Copper promotes arylation and vinylation of a wide range of nitrogen nucleophiles, including amines, nitrogen heterocycles, and amide derivatives. The reactivity profile is complementary to that of palladium and often offers orthogonal chemoselectivity. This chapter presents a thorough overview of the copper‐catalyzed coupling of aryl and vinyl halides with nitrogen nucleophiles. Current understanding of the mechanism of this process is presented along with a detailed overview of the scope and limitations of this reaction along with optimal reaction conditions for the coupling of various nitrogen nucleophile classes.

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Palladium-catalyzed annulation of alkynyl aryl ethers with isocyanates through o-C–H cleavage. Synthesis of solid-state emissive 2-methylidene-2H-1,4-benzoxazin-3(4H)-ones

et al. 2015

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Copper-catalyzed one-pot synthesis of 2H-1,4-benzoxazin-3-(4H)-ones from 2-(o-haloaryloxy)acyl chlorides and primary amines

Cited by 4 publications

References 1 publication

Synthesis, Biological Evaluation, and Structure–Activity Relationships of Potent Noncovalent and Nonpeptidic Cruzain Inhibitors as Anti-Trypanosoma cruzi Agents

Synthesis, Biological Evaluation, and Structure–Activity Relationships of Potent Noncovalent and Nonpeptidic Cruzain Inhibitors as Anti-Trypanosoma cruzi Agents

Copper‐Catalyzed Amination of Aryl and Alkenyl Electrophiles

Palladium-catalyzed annulation of alkynyl aryl ethers with isocyanates through o-C–H cleavage. Synthesis of solid-state emissive 2-methylidene-2H-1,4-benzoxazin-3(4H)-ones

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