<i>N</i>-Mannich Bases of Aromatic Heterocyclic Amides: Synthesis via Copper-Catalyzed Aerobic Cross-Dehydrogenative Coupling under Ambient Conditions

Singh, Shailendra K.; Chandna, Nisha; Jain, Nidhi

doi:10.1021/acs.orglett.7b00125

Cited by 25 publications

(7 citation statements)

References 46 publications

(31 reference statements)

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“…Mechanistic studies performed using isotope‐labeling studies indicate the radical pathway involves iminium ion intermediate (See Figure 29). [70] …”

Section: Copper Catalyzed Synthesis Of Heterocyclic Amidesmentioning

confidence: 99%

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Chandra

2021

ChemistrySelect

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Copper with variable oxidation states, Earth abundance was used as a tunable and multifunctional catalyst promoting organic transformations. Copper‐based catalytic materials have been effectively utilized in bioorganic chemistry, material science, and natural products synthesis. Several organic transformations involving cycloadditions, cyclizations, cross‐couplings, and condensations in one‐pot assist in the formation of multiple bonds like C−C/C−O bonds, C−C/C−N bonds, and C−N/C−S bonds. Copper has recently been explored as efficient catalytic material for the synthesis of heterocyclic amides. Heterocyclic amides are essential organic compounds are quite prevelent in the pharmaceuticals, fine chemicals and natural products. The heterocyclic amides are the key components of multivarious ace drugs and bio‐molecules like peptides and proteins, and several natural products. Therefore, heterocyclic amides are of much significance, and research focusing on the facile methods is of much interest to contemporary synthetic chemists. Different techniques have been developed using copper‐based catalysts for the synthesis of heterocyclic amdes. These heterocyclic amides are prepared by the reaction of C(sp3)−H, C(sp2)−H, C(sp)−H bonds, aldehydes, ketones, carboxylic acid, carboxylic acid‐based surrogates, and amine surrogates. N‐alkyation of amides with multifarious substrates has been the extensively investigated for the synthesis of heterocyclic amides. Finally, multicomponent domino reactions have also been investigated for the synthesis of heterocycic amides. The present review summarises various synthetic techniques for the copper catalyzed heterocyclic amides synthesis.

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“…Mechanistic studies performed using isotope‐labeling studies indicate the radical pathway involves iminium ion intermediate (See Figure 29). [70] …”

Section: Copper Catalyzed Synthesis Of Heterocyclic Amidesmentioning

confidence: 99%

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Chandra

2021

ChemistrySelect

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“…Apparently, the studies with N , N -dimethylbenzylamines are limited to C–C bond-forming reactions only, with no literature precedence on a direct α-amination at the sp 3 carbon. In continuation of our interest in direct C–N bond formations, we explored a N–H/C–H cross-dehydrogenative coupling between azoles and N , N -dimethylbenzylamines using a nanocatalytic system comprising Cu 2 S NPs. The methodology was explored for triazoles ( NH -1,2,3-triazoles, 4-phenyl- NH -1,2,3-triazoles, 1 H -benzotriazoles, and 5,6-dimethyl-1 H -benzotriazoles) and carbazoles as coupling partners (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Regioselective Synthesis ofN²-Alkylated-1,2,3 Triazoles andN¹-Alkylated Benzotriazoles: Cu₂S as a Recyclable Nanocatalyst for Oxidative Amination ofN,N-Dimethylbenzylamines

et al. 2018

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Copper chalcogenide nanoparticles (CuS) synthesized for the first time from a single-source precursor, CuSPh, act as highly efficient and reusable heterogeneous catalyst for regioselective amination of N, N-dimethylbenzylamines with various azoles. The reaction involves N-H/C-H cross-dehydrogenative coupling (CDC) and demonstrates wide functional group tolerance. It provides highly selective access to N-alkylated benzotriazoles, N-alkylated 1,2,3-triazoles and 4-phenyl-1,2,3-triazoles, and N-alkylated carbazoles in 70-89% yields under solvent-free conditions. The CuS nanocatalyst has been characterized by PXRD, XPS, SEM-EDX, and HR-TEM analysis. Mechanistic studies suggest that the reaction follows a radical pathway and involves an iminium ion intermediate.

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“…It is known that Mannich reaction usually is one of important methods to generate various N-or C-Mannich base derivatives based on various intermediates which is frequently used in drug design. [7][8][9][10][11] Because these derivative molecules exhibit good lipophilicity and absorption behavior making them favorable prodrugs under biological conditions; [12] many of the heterocylic Mannich bases display versatile properties such as antifungal, [13] antitumor, [14] antimicrobial, [15] and anticancer [16] agents. The Mannich reaction of the imidazole ring has been investigated since 1940s.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure and Biological Activities of Novel 2‐(Trifluoromethyl)‐ 6‐arylimidazo[2,1‐b][1,3,4]‐thiadiazole (bis‐)Mannich Base Derivatives Containing Substitutedpiperazine Moiety

Zhang

Song

et al. 2018

Chin. J. Chem.

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A convenient and practicable method for the synthesis of the novel 2‐(trifluoromethyl)‐6‐arylimidazo[2,1‐b][1,3,4]‐thiadiazole (bis‐)Mannich base derivatives containing various substitutedpiperazine motif has been developed based on the fused‐heterocycle intermediate. The new structures were identified through melting points, 1H NMR, 13C NMR, 19F NMR, elemental analysis (or HRMS) and X‐ray single‐crystal diffraction. The pesticidal bioassays showed that some of compounds exhibited good fungicidal activities against Cercospora arachidicola, Physalospora piricola and Rhizoctonia cereali at 50 mg/L; some of them displayed favourable insecticidal activities against oriental armyworm (Mythimna separata Walker) at 200 mg/L, particularly, Vk and Vm with mortality rate of 75% and 80% respectively, could be considered as new insecticidal lead compounds for further structural optimization.

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N-Mannich Bases of Aromatic Heterocyclic Amides: Synthesis via Copper-Catalyzed Aerobic Cross-Dehydrogenative Coupling under Ambient Conditions

Cited by 25 publications

References 46 publications

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Regioselective Synthesis ofN²-Alkylated-1,2,3 Triazoles andN¹-Alkylated Benzotriazoles: Cu₂S as a Recyclable Nanocatalyst for Oxidative Amination ofN,N-Dimethylbenzylamines

Synthesis, Structure and Biological Activities of Novel 2‐(Trifluoromethyl)‐ 6‐arylimidazo[2,1‐b][1,3,4]‐thiadiazole (bis‐)Mannich Base Derivatives Containing Substitutedpiperazine Moiety

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N-Mannich Bases of Aromatic Heterocyclic Amides: Synthesis via Copper-Catalyzed Aerobic Cross-Dehydrogenative Coupling under Ambient Conditions

Cited by 25 publications

References 46 publications

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Regioselective Synthesis ofN2-Alkylated-1,2,3 Triazoles andN1-Alkylated Benzotriazoles: Cu2S as a Recyclable Nanocatalyst for Oxidative Amination ofN,N-Dimethylbenzylamines

Synthesis, Structure and Biological Activities of Novel 2‐(Trifluoromethyl)‐ 6‐arylimidazo[2,1‐b][1,3,4]‐thiadiazole (bis‐)Mannich Base Derivatives Containing Substitutedpiperazine Moiety

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Regioselective Synthesis ofN²-Alkylated-1,2,3 Triazoles andN¹-Alkylated Benzotriazoles: Cu₂S as a Recyclable Nanocatalyst for Oxidative Amination ofN,N-Dimethylbenzylamines