Synthesis of 2‐formyl‐1‐aza‐dibenzo[<i>e</i>,<i>h</i>]azulenes

Pešić, Dijana; Landek, Ivana Ozimec; Čikoš, Ana; Metelko, Biserka; Gabelica, Vesna; Stanić, Barbara; Merćep, Mladen; Mesić, Milan

doi:10.1002/jhet.5570440524

Cited by 8 publications

(2 citation statements)

References 17 publications

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“…In the case of 4-[5-(4-fluorophenyl)-4-pyridine-4-yl-1H-pyrrol-2-yl]-1-methyl-piperidine-4-ol 41 [49], biological activity was confirmed with an IC50 value of 0.13 µM. However, 1H-8-oxa-1-aza-dibenzo[e,h]azulen1H-dibenzo[2,3:6,7]azepino [4,5-b]pyrrol [51,53] was not detected (IC50 > 10 µmol dm −3 ), indicating a lack of inhibitory activity. Table S1 in the Supplementary materials presents data collected by the authors of the article [49] on the inhibitory activity of 4-[5-(4-fluorophenyl)-4-pyridine-4-yl-1H-pyrrol-2-yl]-1-methyl-piperidine-4-ol derivatives, including DMHG, along with other heterocycles of similar structures.…”

Section: Dmhg In the Directed Synthesis Of Biologically Active Analog...mentioning

confidence: 98%

“…Attempts have been made to synthesize inhibitors of p38 MAP kinases (mitogenactivated protein kinases) based on DMHG [49][50][51], aiming to reduce the production of pro-inflammatory cytokines, which contribute to tissue destruction in diseases such as rheumatoid arthritis, an inflammatory joint disease. In one method [49] (Figure 6), the authors propose a DMHG-based condensation in an alkaline medium, alcohol solution, without the use of organometallic reagents.…”

Section: Dmhg In the Directed Synthesis Of Biologically Active Analog...mentioning

confidence: 99%

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The Recycling of Substandard Rocket Fuel N,N-Dimethylhydrazine via the Involvement of Its Hydrazones Derived from Glyoxal, Acrolein, Metacrolein, Crotonaldehyde, and Formaldehyde in Organic Synthesis

Ivanova,

Osipova,

Vasilieva

et al. 2023

IJMS

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“Heptil” (unsymmetrical dimethylhydrazine—UDMH) is extensively employed worldwide as a propellant for rocket engines. However, UDMH constantly loses its properties as a result of its continuous and uncontrolled absorption of moisture, which cannot be rectified. This situation threatens its long-term usability. UDMH is an exceedingly toxic compound (Hazard Class 1), which complicates its transportation and disposal. Incineration is currently the only method used for its disposal, but this process generates oxidation by-products that are even more toxic than the original UDMH. A more benign approach involves its immediate reaction with a formalin solution to form 1,1–dimethyl-2-methylene hydrazone (MDH), which is significantly less toxic by an order of magnitude. MDH can then be polymerized under acidic conditions, and the resulting product can be burned, yielding substantial amounts of nitrogen oxides. This review seeks to shift the focus of MDH from incineration towards its application in the synthesis of relatively non-toxic and readily available analogs of various pharmaceutical substances. We aim to bring the attention of the international chemical community to the distinctive properties of MDH, as well as other hydrazones (such as glyoxal, acrolein, crotonal, and meta-crolyl), wherein each structural fragment can initiate unique transformations that have potential applications in molecular design, pharmaceutical research, and medicinal chemistry.

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Section: Dmhg In the Directed Synthesis Of Biologically Active Analog...mentioning

confidence: 98%

Section: Dmhg In the Directed Synthesis Of Biologically Active Analog...mentioning

confidence: 99%

The Recycling of Substandard Rocket Fuel N,N-Dimethylhydrazine via the Involvement of Its Hydrazones Derived from Glyoxal, Acrolein, Metacrolein, Crotonaldehyde, and Formaldehyde in Organic Synthesis

Ivanova,

Osipova,

Vasilieva

et al. 2023

IJMS

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ChemInform Abstract: Synthesis of 2‐Formyl‐1‐aza‐dibenzo[e,h]azulenes.

et al. 2008

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Novel tetracyclic imidazole derivatives: Synthesis, dynamic NMR study, and anti‐inflammatory evaluation

Rupčić

Modrić

Hutinec

et al. 2010

Journal of Heterocyclic Chem

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A series of tetracyclic imidazole derivatives 9a-9v and 10a-10h are prepared by multistep route starting from the known tricyclic diketones 2a-2d. Intermediary dibenzooxepin [4,5-d]imidazoles (3a, 3c) and dibenzothiepin [4,5-d]imidazoles (3b, 3d) are N-protected to 4e, 4f and to the isomeric compounds 5a, 5b and 6a, 6b. The isomeric compounds 5 and 6 are separated. Compounds 4, 5, and 6 are formylated at C(2) to afford 7a-7j. In the last steps, aldehyde group is reduced, then alkylated to the two sets of isomeric x-dimethylaminoalkyl derivatives 9a-9v. N-deprotection of 9i-9v led to the compounds 10a-10h. Assignment of the syn/anti structure to 5a and 6a was supported by 1D selective ROESY NMR spectra, whereas conformational mobility for the selected representatives 8a and 8b is studied by dynamic NMR. Activation energies (energy barriers for interconversion) are determined to be $11.5 and 16.2 kcal/mol, respectively. A series of derivatives 9 and 10 were tested in vitro for their antiinflammatory activity.

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Synthesis of 2‐formyl‐1‐aza‐dibenzo[e,h]azulenes

Cited by 8 publications

References 17 publications

The Recycling of Substandard Rocket Fuel N,N-Dimethylhydrazine via the Involvement of Its Hydrazones Derived from Glyoxal, Acrolein, Metacrolein, Crotonaldehyde, and Formaldehyde in Organic Synthesis

The Recycling of Substandard Rocket Fuel N,N-Dimethylhydrazine via the Involvement of Its Hydrazones Derived from Glyoxal, Acrolein, Metacrolein, Crotonaldehyde, and Formaldehyde in Organic Synthesis

ChemInform Abstract: Synthesis of 2‐Formyl‐1‐aza‐dibenzo[e,h]azulenes.

Novel tetracyclic imidazole derivatives: Synthesis, dynamic NMR study, and anti‐inflammatory evaluation

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