Synthesis, Spectroscopic, X-ray Diffraction and DFT Studies of Novel Benzimidazole Fused-1,4-Oxazepines

Almansour, Abdulrahman I.; Arumugam, Natarajan; Soliman, Saied M.; Altaf, Mohammad; Ghabbour, Hazem A.

doi:10.3390/molecules21060724

Cited by 11 publications

(3 citation statements)

References 34 publications

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“…InCl 3 -catalyzed the synthesis of benzimidazole-fused 1,4-oxazepines by intramolecular addition of a pendant alcohol onto an in situ-generated imine ( Scheme 26 ) [ 87 ].…”

Section: Syntheses Of Ring-fused Benzimidazoles and Imidazobenzimidazolesmentioning

confidence: 99%

Advances in the Synthesis of Ring-Fused Benzimidazoles and Imidazobenzimidazoles

et al. 2021

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This review article provides a perspective on the synthesis of alicyclic and heterocyclic ring-fused benzimidazoles, imidazo[4,5-f]benzimidazoles, and imidazo[5,4-f]benzimidazoles. These heterocycles have a plethora of biological activities with the iminoquinone and quinone derivatives displaying potent bioreductive antitumor activity. Synthesis is categorized according to the cyclization reaction and mechanisms are detailed. Nitrobenzene reduction, cyclization of aryl amidines, lactams and isothiocyanates are described. Protocols include condensation, cross-dehydrogenative coupling with transition metal catalysis, annulation onto benzimidazole, often using CuI-catalysis, and radical cyclization with homolytic aromatic substitution. Many oxidative transformations are under metal-free conditions, including using thermal, photochemical, and electrochemical methods. Syntheses of diazole analogues of mitomycin C derivatives are described. Traditional oxidations of o-(cycloamino)anilines using peroxides in acid via the t-amino effect remain popular.

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“…InCl 3 -catalyzed the synthesis of benzimidazole-fused 1,4-oxazepines by intramolecular addition of a pendant alcohol onto an in situ-generated imine ( Scheme 26 ) [ 87 ].…”

Section: Syntheses Of Ring-fused Benzimidazoles and Imidazobenzimidazolesmentioning

confidence: 99%

Advances in the Synthesis of Ring-Fused Benzimidazoles and Imidazobenzimidazoles

et al. 2021

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“…The effects of the molecular structure on chemical reactivity have been studied extensively [53–57]. Quantum chemical indices calculated to predict that a compound is fitted to be a corrosion inhibitor are: energy of the highest occupied molecular orbital (E HOMO ), energy of the lowest unoccupied molecular orbital (E LUMO ), dipole moment (μ), polarizability (α), total natural charges (Q total ), total Mulliken charges (Z total ), adiabatic ionization potential (I a ), adiabatic electron affinity (A a ), Molar volume (V i ), aromaticity-magnetism based on Nuclear Independent Chemical Shift (NICS), the number of electrons transferred (ΔN) and electrophilicity index (ω a ) [52, 58–71]. The radial distribution function (RDF) study confirmed that both the neutral and protonated form of the inhibitor show significant interaction with the steel surface.…”

Section: Benzimidazoles As Corrosion Inhibitors For Other Metalsmentioning

confidence: 99%

Recent advances in the use of benzimidazoles as corrosion inhibitors

Marinescu

2019

BMC Chemistry

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BackgroundBenzimidazole, a key heterocycle in therapeutic chemistry, and its derivatives, are recently mentioned in the literature as corrosion inhibitors for steels (CS, MS), pure metals (Fe, Al, Cu, Zn) and alloys. Benzimidazoles are good corrosion inhibitors for extremely aggressive, corrosive acidic media such as 1 M HCl, 1 M HNO3, 1.5 M H2SO4, basic media, 0.1 M NaOH or salt solutions. Benzimidazole derivatives act as mixed type inhibitors, exhibiting stronger inhibitive effect on the cathodic reaction than on the anodic one.ConclusionThese review highlights recent research in the field of benzimidazole compounds that their role as corrosion inhibitors, the structure of the compounds, electrochemical studies, the experimental conditions, the proposed mechanisms as well as the quantum theoretical studies that predict the structure of the compounds with inhibition properties.

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“…It is hypothesized that the reaction of oxazole 21 with Grignard or organolithium reagent produced an inactive dianion by deprotonation of both the indole NH and the active methylene group. Water addition to, or epoxidation of, the isopropylidene double bond in labradorin 5 (22) was unsuccessful with various reagents, such as H 2 SO 4 /H 2 O at room temperature, 17 polyphosphoric acid (PPA) at 90 °C, 18 Hg(OAc) 2 /THF-H 2 O then NaOH/NaBH 4 , 19 HCl/THF-H 2 O at reflux, 20 and meta-chloroperoxybenzoic acid (mCPBA) at 0 °C. 21 Finally, upon treatment of labradorin 5 (22) with 50% aqueous H 2 SO 4 in boiling 1,4-dioxane 22 for 4 days, pimprinol B (2) was produced with 15% conversion and in 11% isolated yield.…”

Section: Paper Syn Openmentioning

confidence: 99%

Total Synthesis of Bacterial 5-(3-Indolyl)oxazole Alkaloids: Pimprinols A–C

Szabó¹,

Kormány²,

Dancsó³

et al. 2019

SynOpen

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Pimprinols A, B, and C are bacterial 5-(3-indolyl)oxazole alkaloids that have been isolated from Streptomyces sp. Lv3–13. In this paper, we report a new synthesis of pimprinol A and the first total synthesis of pimprinol B and pimprinol C. In addition, antipodes of the naturally occurring pimprinols A and C, as well as the racemates of these two alkaloids were also prepared. In the pivotal step, the 1,3-oxazole ring was constructed by a Nicolaou’s modified Robinson–Gabriel cyclization.

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Synthesis, Spectroscopic, X-ray Diffraction and DFT Studies of Novel Benzimidazole Fused-1,4-Oxazepines

Cited by 11 publications

References 34 publications

Advances in the Synthesis of Ring-Fused Benzimidazoles and Imidazobenzimidazoles

Advances in the Synthesis of Ring-Fused Benzimidazoles and Imidazobenzimidazoles

Recent advances in the use of benzimidazoles as corrosion inhibitors

Total Synthesis of Bacterial 5-(3-Indolyl)oxazole Alkaloids: Pimprinols A–C

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