“All-water” chemistry of tandem N-alkylation–reduction–condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles
Literature Information
Damodara N. Kommi, Dinesh Kumar, Rohit Bansal, Rajesh Chebolu, Asit K. Chakraborti
A water-assisted tandem N-alkylation–reduction–condensation process has been devised as a new synthetic route for the one-pot synthesis of N-arylmethyl-2-substituted benzimidazoles. Water plays the crucial and indispensable role through hydrogen bond mediated ‘electrophile–nucleophile dual activation’ in promoting selective N-monobenzylation of o-nitroanilines as an alternative to the transition metal-based chemistry for C–N bond formation (amination) and forms the basis of disposing the substituents on the benzimidazole moiety in regiodefined manner. Water also exerts a beneficial effect in the condensation of N-monobenzylated o-phenylenediamines with aldehydes. The water-assisted C–N bond formation chemistry led to metal/base-free synthesis of N-monobenzylated o-nitroanilines and N-monobenzylated o-phenylenediamines. The indispensable/advantageous role of water in the various stage of the N-alkylation–reduction–condensation process exemplifies an ‘all-water’ chemistry for the synthesis of N-arylmethyl-2-substituted benzimidazoles.
Recommended Journals

Environmental Toxicology and Pharmacology

Molecular Diversity

Photochemical & Photobiological Sciences

Nature Reviews Drug Discovery

Faraday Discussions

Journal of Medical Biochemistry

Journal of Enzyme inhibition and Medicinal Chemistry

Coloration Technology

Green Chemistry

European Journal of Organic Chemistry
Related Literature
Nano-size scaling of alloy intra-particle vs. inter-particle separation transitions: prediction of distinctly interface-affected critical behaviour
M. Polak, L. Rubinovich
DOI: 10.1039/C6CP02444K
Confined water in imidazolium based ionic liquids: a supramolecular guest@host complex case
Marcileia Zanatta, Anne-Lise Girard, Graciane Marin, Gunter Ebeling, Francisco P. dos Santos, Chiara Valsecchi, Hubert Stassen, Paolo R. Livotto, William Lewis
DOI: 10.1039/C6CP03112A
Revealing electronic structure changes in Chevrel phase cathodes upon Mg insertion using X-ray absorption spectroscopy
Liwen F. Wan, Joshua Wright, Brian R. Perdue, Timothy T. Fister, Soojeong Kim, Christopher A. Apblett, David Prendergast
DOI: 10.1039/C6CP02412B
In situ investigation of mesoporous silicon oxidation kinetics using infrared emittance spectroscopy
Benjamin Bardet, Domingos De Sousa Meneses, Thomas Defforge, Jérôme Billoué, Gaël Gautier
DOI: 10.1039/C6CP02086K
Study of the reactivity of silica supported tantalum catalysts with oxygen followed by in situ HEROS
Wojciech Błachucki, Yves Kayser, Jean-Claude Dousse, Joanna Hoszowska, Daniel L. A. Fernandes
DOI: 10.1039/C5CP02950C
Heads or tails: how do chemically substituted fullerenes melt?
DOI: 10.1039/C6CP01333C
Surface adsorption of sulfonated poly(phenylene sulfone)/C14TAB mixtures and its correlation with foam film stability
Martin Uhlig, Reinhard Miller, Regine von Klitzing
DOI: 10.1039/C6CP02256A
New ester based gemini surfactants: the effect of different cationic headgroups on micellization properties and viscosity of aqueous micellar solution
Avinash Bhadani, Misako Tani, Takeshi Endo, Kenichi Sakai, Masahiko Abe, Hideki Sakai
DOI: 10.1039/C5CP02115D
Spectacular enhancement of thermoelectric phenomena in chemically synthesized graphene nanoribbons with substitution atoms
K. Zberecki, R. Swirkowicz, M. Wierzbicki
DOI: 10.1039/C6CP02877B
You might also like
What regulatory guidelines apply to 4-Amino-3-bromophenol (CAS: 74440-80-5)?
4-Amino-3-bromophenol (CAS: 74440-80-5) falls under the classification of a haza...
How should (17beta)-3-Oxoestr-4-en-17-yl acetate (CAS: 1425-10-1) be stored?
(17beta)-3-Oxoestr-4-en-17-yl acetate should be stored in a cool, dry place away...
What are the physical and chemical properties of 2-[(2,2-Diethoxyethyl)disulfanyl]-1,1-diethoxyethane (CAS: 76505-71-0)?
2-[(2,2-Diethoxyethyl)disulfanyl]-1,1-diethoxyethane (CAS: 76505-71-0) is a colo...
What is the market or research trend for 1-(β-D-ribofuranosyl)-1H-imidazo[4,5-c]pyridin-4-amine?
The market and research for 1-(β-D-ribofuranosyl)-1H-imidazo[4,5-c]pyridin-4-ami...
How should waste containing Conjugated Estrogen (CAS: 12126-59-9) be handled?
Waste containing Conjugated Estrogen (CAS: 12126-59-9) should be collected and d...
What is the market or research trend for Bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate?
The market for Bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate (CAS...
Are there alternatives to 3,4'-Di-O-methylellagic acid (CAS: 57499-59-9) in synthesis?
There are several alternatives to 3,4'-Di-O-methylellagic acid (CAS: 57499-59-9)...
What regulatory guidelines apply to 2-Chloro-N,N-dimethylpyridin-4-amine (CAS: 59047-70-0)?
2-Chloro-N,N-dimethylpyridin-4-amine (CAS: 59047-70-0) is regulated under the Gl...
What is cerium(3+);oxygen(2-);vanadium(5+) (CAS: 13597-19-8)?
Cerium(3+);oxygen(2-);vanadium(5+) (CAS: 13597-19-8) is a complex inorganic comp...
Is 7-Chloro-1-iodoisoquinoline (CAS: 1203579-27-4) safe?
7-Chloro-1-iodoisoquinoline (CAS: 1203579-27-4) is generally considered safe whe...
Source Journal
Green Chemistry

Green Chemistry provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on, but not limited to, the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998). Green chemistry is the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry is at the frontiers of this continuously-evolving interdisciplinary science and publishes research that attempts to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. Submissions on all aspects of research relating to the endeavour are welcome. The journal publishes original and significant cutting-edge research that is likely to be of wide general appeal. To be published, work must present a significant advance in green chemistry. Papers must contain a comparison with existing methods and demonstrate advantages over those methods before publication can be considered. For more information please see this Editorial. Coverage includes the following, but is not limited to: Design (e.g. biomimicry, design for degradation/recycling/reduced toxicity…) Reagents & Feedstocks (e.g. renewables, CO2, solvents, auxiliary agents, waste utilization…) Synthesis (e.g. organic, inorganic, synthetic biology…) Catalysis (e.g. homogeneous, heterogeneous, enzyme, whole cell…) Process (e.g. process design, intensification, separations, recycling, efficiency…) Energy (e.g. renewable energy, fuels, photovoltaics, fuel cells, energy storage, energy carriers…) Applications (e.g. electronics, dyes, consumer products, coatings, pharmaceuticals, preservatives, building materials, chemicals for industry/agriculture/mining…) Impact (e.g. safety, metrics, LCA, sustainability, (eco)toxicology…) Green chemistry is, by definition, a continuously-evolving frontier. Therefore, the inclusion of a particular material or technology does not, of itself, guarantee that a paper is suitable for the journal. To be suitable, the novel advance should have the potential for reduced environmental impact relative to the state of the art. Green Chemistry does not normally deal with research associated with 'end-of-pipe' or remediation issues.


![4-{2-[(9H-Fluoren-9-ylmethoxy)carbonyl]hydrazino}benzoic acid structure 4-{2-[(9H-Fluoren-9-ylmethoxy)carbonyl]hydrazino}benzoic acid structure](https://static.chemtradehub.com/structs/214/214475-53-3-bf36.webp)

