Synthesis of 2,2-Dimethylhydrazonebut-2-enenitriles and [(2,2-Dimethylhydrazono)methyl]phenylacrylonitriles for Development of Antimicrobial Fluorescent Dyes

Mar’yasov, M. A.; Davydova, V. V.; Насакин, О. Е.; Shteingolts, Sergey A.; Лодочникова, О. А.

doi:10.1134/s1070363221090024

Cited by 3 publications

(4 citation statements)

References 11 publications

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“…The MDH-reaction at the CH-acidic center enables the incorporation of MDH in the synthesis with tetracyanoethane (TCNEH2). In contrast to our previous publication [29], which described the addition of MDH to tetracyanoethylene (TCNE) through methyleneactive hydrogen, the reaction of MDH with TCNEH2 leads to the formation of cyclic pyrrole derivative 12, as depicted in the proposed chemical transformation scheme presented below (Figure 14). As mentioned above (Section 1), the resulting products 9a,b, 9′, 12c, 8 contain the moieties that are similar with the structures of well-known drugs used for the treatment As mentioned above (Section 1), the resulting products 9a,b, 9 , 12c, 8 contain the moieties that are similar with the structures of well-known drugs used for the treatment of neurodegenerative and viral diseases.…”

Section: Discussionmentioning

confidence: 72%

“…As mentioned above (Section 1), the resulting products 9a,b, 9′, 12c, 8 contain the moieties that are similar with the structures of well-known drugs used for the treatment The MDH-reaction at the CH-acidic center enables the incorporation of MDH in the synthesis with tetracyanoethane (TCNEH 2 ). In contrast to our previous publication [29], which described the addition of MDH to tetracyanoethylene (TCNE) through methyleneactive hydrogen, the reaction of MDH with TCNEH 2 leads to the formation of cyclic pyrrole derivative 12 (m/z 203.1047) (see Figure S18 in Supplementary Materials), as depicted in the proposed chemical transformation scheme presented below (Figure 14). DMH reacts with the tetracyanoethylene (TCNE) released at the hydrogen atom of the methylene group.…”

Section: Discussionmentioning

confidence: 73%

“…DMH reacts with the tetracyanoethylene (TCNE) released at the hydrogen atom of the methylene group. In our earlier publication [29], we reported that the low-yield tricyanohydrazine derivatives 9 were obtained, known as potential antimicrobial dyes and photosensitizers (Figure 13). The MDH-reaction at the CH-acidic center enables the incorporation of MDH in the synthesis with tetracyanoethane (TCNEH2).…”

Section: Discussionmentioning

confidence: 97%

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Treatment of Substandard Rocket Fuel 1,1-Dimethylhydrazine via Its Methylene Derivative into Heterocycles Based on Pyrrolo-[3,4c]Quinolines, Cyclododeca[b]piran and Pyrrole

Ivanova,

Maryasov,

Andreeva

et al. 2023

IJMS

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1,1-Dimethylhydrazine (Heptil, rocket fuel (UDMH)) is characterized by extremely high toxicity, teratogenicity and the ability to constantly absorb water from the atmosphere, losing its energy characteristics. In this regard, as well as due to the alternative fuel (“Angara”) transition, there is a need for UDMH utilization in huge amounts. 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 a substantial amount of nitrogen oxides. We propose an alternative to incineration by involving MDH in organic synthesis. We studied the reactions of MDH and its analog N,N-dimethyl-2-(methylenamino)ethane-1-amine (MDEA) with available CH-acids: tetracyanoethylated ketones (TCEKs) based on cyclohexanone, 4-propylcyclohexanone, 2-methylcyclohexanone, cyclododecanone and tetracyanoethane. The structures synthesized were confirmed by IR, 1H, 13C NMR and mass spectroscopy methods. MDH-based adducts were also identified by X-ray structural analysis. TCEKs and MDH, as well as TCEK based on cyclohexanone and MDEA, form bi- and tricyclic structures: pyrrolo [3,4c]-quinolines (using TCEKs based on cyclohexanone and 4-propylcyclohexanone), epiminomethanoquinoline-3,4-dicarbonitrile (using TCEK based on 2-methylcyclohexanone) and cyclododec[b]pyran-3,4-dicarbonitrile (using TCEK based on cyclododecanone). MDH and TCNEH2 formed a pyrrole derivative. Thus, we synthesized the structures that are of interest for molecular design and pharmaceutical chemistry.

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Section: Discussionmentioning

confidence: 72%

Section: Discussionmentioning

confidence: 73%

Section: Discussionmentioning

confidence: 97%

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Treatment of Substandard Rocket Fuel 1,1-Dimethylhydrazine via Its Methylene Derivative into Heterocycles Based on Pyrrolo-[3,4c]Quinolines, Cyclododeca[b]piran and Pyrrole

Ivanova,

Maryasov,

Andreeva

et al. 2023

IJMS

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“…Likewise, the compound based on dimethylhexahydroxyflavylium (DMHG) [16] was employed to synthesize optically pure polymetinnitrile dyes, which hold potential as photosensitizers for antimicrobial photodynamic therapy.…”

Section: Stereoselectivity Of Dmhgmentioning

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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“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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Synthesis and Photophysical Properties of Donor-Acceptor Triene Derivatives of Malononitrile Dimer

Shishlikova,

Khakimova,

Ershov

2024

Russ J Gen Chem

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Synthesis of 2,2-Dimethylhydrazonebut-2-enenitriles and [(2,2-Dimethylhydrazono)methyl]phenylacrylonitriles for Development of Antimicrobial Fluorescent Dyes

Cited by 3 publications

References 11 publications

Treatment of Substandard Rocket Fuel 1,1-Dimethylhydrazine via Its Methylene Derivative into Heterocycles Based on Pyrrolo-[3,4c]Quinolines, Cyclododeca[b]piran and Pyrrole

Treatment of Substandard Rocket Fuel 1,1-Dimethylhydrazine via Its Methylene Derivative into Heterocycles Based on Pyrrolo-[3,4c]Quinolines, Cyclododeca[b]piran and Pyrrole

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

Synthesis and Photophysical Properties of Donor-Acceptor Triene Derivatives of Malononitrile Dimer

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