An expeditious synthetic protocol for chlorination of imidazole N-oxide: Synthesis of 2-chloroimidazoles

Hossain, Mossaraf; Pradhan, Kiran; Nanda, Ashis Kumar

doi:10.1016/j.tetlet.2017.08.047

Cited by 15 publications

(10 citation statements)

References 11 publications

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“…N-((6-bromo-1H-benzo[d]imidazol-2-yl) methyl)-4-chloroaniline.Puratchikody A. et al reported 2-substituted-4, 5-diphenyl-1H-imidazoles and their anti-inflammatory activity of this compound were examined by using Carrageenan-induced paw edema method. Finally found the maximum activity of this compound with reference as an indomethacin drug[48].…”

mentioning

confidence: 81%

“…The method has been examined with differently substituted N-phenyl ring. The derivatives of 2-chlorinated imidazole moiety are very useful precursors and subunits of numerous pharmacologically important drugs [48]. In 2018, R Thomas and co-workers reveals the comparison study via experimentally and computationally with the 2-chloroimidazole derivatives, besides spectroscopy techniques such as IR, FT-Raman and NMR, reactivity study also done based on density functional theory (DFT) calculations, molecular electrostatic potential (MEP), average local ionization energy (ALIE) values, bond dissociation energies (BDE) and Fukui functions.…”

Section: Development Of the Synthesis Of Imidazolesmentioning

confidence: 99%

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A Review on Heterocyclic: Synthesis and Their Application in Medicinal Chemistry of Imidazole Moiety

Hossain¹,

Nanda²

2018

SJC

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In an organic chemistry, largest families of organic compounds are belongs in the heterocyclic compounds. In our daily life important of heterocyclic compounds are of very essential. It has broad range of application in medicinal chemistry and in agrochemicals products. Applications are also found in as developers, as corrosion inhibitors, sanitizers, as copolymers, antioxidants, dye stuff. There is always an important thing about an efficient methodology for synthesizing of new heterocycles moiety. Now in literature survey reveals that more than 85-95% new drugs containing heterocycles which has bright scientific insight in the biological system. In this review work, I mainly focus such type of heterocycle and their families which has main utility in medicinal chemistry. In the recent past developments of imidazole-based compounds in the wide range of medicinal chemistry such as antihypertensive, antineuropathic, antitubercular, antiviral, anti-inflammatory, antibacterial, antiobesity, antiparasitic, antifungal, antihistaminic, anticancer, and other potential medicinal agents with their broad applications in pathology and diagnostics. Derivatives of imidazole have placed a unique position in the medicinal chemistry field. The involvement of the imidazole scaffold is a key of synthetic strategy in the drug discovery system. The imidazole moiety is a part of several important naturally occurring products, including histamine, purine, nucleic acid and histidine. It is expected that this brief review could be attractive for new thoughts from academia and pharmaceutical industries to designs of more biologically active and non-toxic imidazole-based drugs. The aims of this review work to the reported imidazole derivatives with pharmaceuticals activity during the past years.

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confidence: 81%

Section: Development Of the Synthesis Of Imidazolesmentioning

confidence: 99%

A Review on Heterocyclic: Synthesis and Their Application in Medicinal Chemistry of Imidazole Moiety

Hossain¹,

Nanda²

2018

SJC

Self Cite

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“…For more insight on the diversity of the catalyst, the reaction was studied with different substrates varying in the nature of the substituent, i.e., electron withdrawing and electron donating ( fig. 3) at optimised condition [33]. Both types of the substituent responded appreciably in this reaction condition.…”

Section: Fig 3: Substrate Scope Of Alumina Catalyst Substituted-3-(bmentioning

confidence: 73%

ALUMINA CATALYST: SYNTHESIS OF NOVEL QUINAZOLINE DERIVATIVES AND THEIR SOLUBILITY INCREASES THROUGH INCLUSION WITH Β-Cyclodextrin

Hossain

Nanda²

2018

Int J Pharm Pharm Sci

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Objective: To synthesis a novel methodology of bioactive quinazoline derivatives under greener process to an excellent yields and increases their solubility via inclusion with β-cyclodextrin (CD). Methods: Derivatives of quinazoline compounds were prepared by the mixture of 3-amino-2-phenylquinazolin-4(3H)-one, derived from 2-phenyl-4H-benzo[1,3]oxazin-4-one by refluxing with hydrazine, substituted aromatic aldehyde and alumina intimately in an agate mortar and pestle under solvent-free condition. Using various techniques for preparing inclusion complexes, kneaded method is the best method for encapsulation in host-guest complex chemistry. All compounds including inclusion complexes were characterised by spectral methods. Results: Synthesized a series of novel quinazoline compounds under a very easier greener process with a commercially available reagent. However, their low bioavailability, due to low absorption and solubility, can limit their potential applications. CD was used to resolve this solubility problem. CD can easily accommodated the guest molecules to encapsulate inside its cavity due to interior the hydrophobic nature with a hydrophilic exterior part to form thermodynamically more stable molecular microcapsules, commonly name as host-guest complexes or inclusion complexes. In this sense, CD was utilized to enhance not only the solubility and bioavailability of these quinazoline compounds but also their antibacterial capacity. The formation of inclusion complex was thus confirmed by ultraviolet-visible spectroscopy (UV-VIS), Fourier Transform Infrared Spectrometry (FT-IR), differential scanning calorimetry (DSC) and solubility study technique. Conclusion: Here we have successfully unfolded an eco-friendly methodology for the synthesis of derivatives of quinazoline and increased their solubility via host-guest inclusion technique. From the spectral analysis, it was concluded that the quinazoline compound is fully encapsulated inside the cavity of the CD.

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“…Hossain and co‐workers used oxalyl chloride to develop the expeditious and greener synthesis of 2‐chloroimidazoles 125 . By simple mixing of the imidazole N ‐oxide 124 with oxalyl chloride in an agate mortar and pestle in the open air in the presence of Et 3 N as a base at room temperature under solvent‐free conditions, the expected 2‐chloroimidazoles were obtained in excellent yields (Scheme ) …”

Section: Deoxygenative Chlorinationmentioning

confidence: 99%

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Mohammadkhani

Heravi

2019

ChemistrySelect

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Oxalyl chloride, (COCl)2, as an inexpensive commercially available chemical is one of the most versatile applicable organic reagents in chemical transformations. It is also employed extensively in various chemical industries. It is employed in various chemical transformations such as chlorination, oxidation, reduction, dehydration, decarboxylation, and formylation reactions as well as ring cleavage of epoxides. During the past decades, numerous procedures using (COCl)2 as reagent have been developed and published. However, its importance has largely been overlooked by the absence of a comprehensive review in chemical literature dealing with its application in organic transformations and its utilization in the chemical industry. This Review aims to provide an overview for the applications of oxalyl chloride in organic synthesis, including its physical properties, synthesis, as well as its unique roles as the reagent in organic reactions, covering the literature over the past 103 years (from 1916 to date).

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An expeditious synthetic protocol for chlorination of imidazole N-oxide: Synthesis of 2-chloroimidazoles

Cited by 15 publications

References 11 publications

A Review on Heterocyclic: Synthesis and Their Application in Medicinal Chemistry of Imidazole Moiety

A Review on Heterocyclic: Synthesis and Their Application in Medicinal Chemistry of Imidazole Moiety

ALUMINA CATALYST: SYNTHESIS OF NOVEL QUINAZOLINE DERIVATIVES AND THEIR SOLUBILITY INCREASES THROUGH INCLUSION WITH Β-Cyclodextrin

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

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