Copper-Catalyzed Inter- and Intramolecular C–N Bond Formation: Synthesis of Benzimidazole-Fused Heterocycles

Rasheed, Sk.; Rao, D. Nageswar; Das, Parthasarathi

doi:10.1021/acs.joc.5b01396

Cited by 75 publications

(19 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2015, Das and co-workers reported the synthesis of various benzimidazole-fused heterocycles via a Cu(II)-catalyzed, inter/intramolecular C-N bond-forming reaction. 75 The one-pot reaction of 2-aminoheteroarenes and 2-iodoarylboronic acids furnished a wide range of benzimidazolefused N-heteroarenes, such as benzimidazo […”

Section: Scheme 83 Possible Catalytic Pathway For the Selective N-arymentioning

confidence: 99%

Advances in Carbon–Element Bond Construction under Chan–Lam Cross-Coupling Conditions: A Second Decade

et al. 2020

Self Cite

View full text Add to dashboard Cite

Copper-mediated carbon–heteroatom bond-forming reactions involving a wide range of substrates have been in the spotlight for many organic chemists. This review highlights developments between 2010 and 2019 in both stoichiometric and catalytic copper-mediated reactions, and also examples of nickel-mediated reactions, under modified Chan–Lam cross-coupling conditions using various nucleophiles; examples include chemo- and regioselective N-arylations or O-arylations. The utilization of various nucleophiles as coupling partners together with reaction optimization (including the choice of copper source, ligands, base, and other additives), limitations, scope, and mechanisms are examined; these have benefitted the development of efficient and milder methods. The synthesis of medicinally valuable or pharmaceutically important nitrogen heterocycles, including isotope-labeled compounds, is also included. Chan–Lam coupling reaction can now form twelve different C–element bonds, making it one of the most diverse and mild reactions known in organic chemistry.1 Introduction2 Construction of C–N and C–O Bonds2.1 C–N Bond Formation2.1.1 Original Discovery via Stoichiometric Copper-Mediated C–N Bond Formation2.1.2 Copper-Catalyzed C–N Bond Formation2.1.3 Coupling with Azides, Sulfoximines, and Sulfonediimines as Nitrogen Nucleophiles2.1.4 Coupling with N,N-Dialkylhydroxylamines2.1.5 Enolate Coupling with sp3-Carbon Nucleophiles2.1.6 Nickel-Catalyzed Chan–Lam Coupling2.1.7 Coupling with Amino Acids2.1.8 Coupling with Alkylboron Reagents2.1.9 Coupling with Electron-Deficient Heteroarylamines2.1.10 Selective C–N Bond Formation for the Synthesis of Heterocycle-Containing Compounds2.1.11 Using Sulfonato-imino Copper(II) Complexes2.2 C–O Bond Formation2.2.1 Coupling with (Hetero)arylboron Reagents2.2.2 Coupling with Alkyl- and Alkenylboron Reagents3 C–Element (Element = S, P, C, F, Cl, Br, I, Se, Te, At) Bond Forma tion under Modified Chan–Lam Conditions4 Conclusions

show abstract

Section: Scheme 83 Possible Catalytic Pathway For the Selective N-arymentioning

confidence: 99%

Advances in Carbon–Element Bond Construction under Chan–Lam Cross-Coupling Conditions: A Second Decade

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

“…The reaction has well tolerated variedly substituted starting materials whether aromatic or aliphatic, only in case of triazoles substituted with an acetate group the final product was obtained in 66% yield. An open-flask, one-pot, Cu(II)-catalyzed ligand-free approach towards C–N bond formation was reported by Rasheed et al [116]. The reaction was catalyzed by Cu(OAc) 2 with cesium carbonate as a base under aerobic conditions.…”

Section: Reviewmentioning

confidence: 99%

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

Reen

Kumar

Sharma

2019

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

A comprehensive account of recent advances in the synthesis of imidazopyridines, assisted through transition-metal-catalyzed multicomponent reactions, C–H activation/functionalization and coupling reactions are highlighted in this review article. The basic illustration of this review comprises of schemes with concise account of explanatory text. The schemes depict the reaction conditions along with a quick look into the mechanism involved to render a deep understanding of the catalytic role. At some instances optimizations of certain features have been illustrated through tables, i.e., selectivity of catalyst, loading of the catalyst and percentage yield with different substrates. Each of the reported examples has been rigorously analyzed for reacting substrates, reaction conditions and transition metals used as the catalyst. This review will be helpful to the chemists in understanding the challenges associated with the reported methods as well as the future possibilities, both in the choice of substrates and catalysts. This review would be quite appealing to a wider range of organic chemists in academia and industrial R&D sectors working in the field of heterocyclic syntheses. In a nutshell, this review will be a guiding torch to envisage: (i) the role of various transition metals in the domain dedicated towards method development and (ii) for the modifications needed thereof in the R&D sector.

show abstract

“…reported a novel synthesis of various benzimidazole‐fused heterocycles 42 from the reaction of 2‐aminoheteroarenens 39 and 2‐iodoarylboronic acids 40 by Cu (II)‐catalyzed inter/intra molecular C−N bond formation through a sole combination of Chan‐Lam coupling followed by Ullmann reaction in a concise manner in one‐pot (Scheme ). The generality of this methodology was proved by the synthesis of a variety of benzimidazole‐fused heteroaromatic derivatives like benzo[4,5] imidazo[2,1‐ b ]thiazoles, benzimidazo[1,2‐ a ]quinolones, pyrido[1,2‐ a ] benzimidazole and benzimidazo [1,2‐ a ]pyrazine …”

Section: Synthesis Of Polycyclic Benzimidazolementioning

confidence: 99%

“…pyrazine. [20] Benzo [4,5]imidazo[1,2-c]quinazolin-6-amines 44 and benzo [4,5]imidazo[1,2-c]pyrimidin-1-amines were synthesized from 2-(2-bromophenyl)benzimidazoles and 2-(2-Bromovinyl)benzimidazoles 42 by using CuI as a catalyst in DMF by microwave irradiation in moderate to good yield (Scheme 8). Synthesis of indolo[1,2-c]quinazolin-6-amine could also be synthesized from the reaction of 2-(2-Bromophenyl)indoles with cyanamide under the same condition.…”

Section: Metal Catalyzed Pathmentioning

confidence: 99%

Polycyclic Benzimidazole: Synthesis and Photophysical Properties

Manna¹,

Das

Samanta³

2019

ChemistrySelect

View full text Add to dashboard Cite

Benzimidazole has tremendous application in medicinal chemistry and material science. The fusion of ring/substitution to benzimidazole nucleus produce polycyclic benzimidazole e. g., pyrido[1,2‐a]benzimidazole, benzimidazo[1,2‐a]quinoline, pyrrolo[1,2‐c]benzimidazolequinones (PBIs) and benzimidazo[2,1‐a]isoquinolines and these are the important synthetic strategies in drug discovery. Benzimidazole analogues have versatile therapeutic properties which encouraged the researchers to develop new therapeutic agents. Hence, the synthetic literature survey towards the polycyclic benzimidazole is paramount important. Due to the beautiful fluorescent properties of fused benzimidazole moiety, they are also used in optoelectronics, optical lasers, and organic luminophores. In addition, this scaffold has broad applications in organometallic catalysis, co‐ordination chemistry, and asymmetric catalysis. Herein, we report a vast synthetic route of benzimidazole embedded polyhetrocycles in the last eight years and their photophysical application in the modern research field.

show abstract

Copper-Catalyzed Inter- and Intramolecular C–N Bond Formation: Synthesis of Benzimidazole-Fused Heterocycles

Cited by 75 publications

References 49 publications

Advances in Carbon–Element Bond Construction under Chan–Lam Cross-Coupling Conditions: A Second Decade

Advances in Carbon–Element Bond Construction under Chan–Lam Cross-Coupling Conditions: A Second Decade

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

Polycyclic Benzimidazole: Synthesis and Photophysical Properties

Contact Info

Product

Resources

About