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
Abstract
:1. Introduction
2. Glyoxal Monodimethylhydrazone
2.1. Stereoselectivity of DMHG
2.2. DMHG in the Directed Synthesis of Biologically Active Analogues of Natural Compounds and Potential Drugs
3. Dimethylhydrazones of Acrolein and Crotonal
3.1. DMHA and DMHC in Cycloaddition Reactions
3.2. DMHA and DMHC in Multicomponent Synthesis of Marine Alkaloids
3.3. Unusual DMHA Reaction (Elongation of the Hydrocarbon Chain)
4. Methacrolein Dimethylhydrazone
5. Formaldehyde Dimethylhydrazone
6. Conclusions
- Negative cost of the original unsymmetrical dimethylhydrazine (UDMH);
- Reduced toxicity and less pungent odor of carbonyl derivatives (compared to UDMH itself), facilitating their use in large-scale and multi-stage synthesis;
- The possibility of conducting stereoselective reactions and obtaining optically pure compounds;
- The electron-rich nitrogen–carbon double bond enables various cycloaddition reactions (4+2, 3+2, 2+2) and the synthesis of heterocyclic derivatives with high yields.
- Many heterocyclic compounds based on dimethylhydrazone have demonstrated high antitumor activity (phenanthroline-7-ones), antifungal activity, and antibacterial activity (thiobazidalin derivatives);
- In numerous reactions, target products with quantitative yields have been obtained. For example, dihydropyran, a component of irciniastatins (marine products), can be synthesized via the Diels–Alder reaction with a 100% yield (Eu(hfc)3, room temperature, 15 h). The Povarov reaction can provide a tetrahydroquinoline ring, which is a constituent of benzostatins. However, one of the main drawbacks of using DMH carbonyl derivatives in organic synthesis is the requirement for hard-to-access reagents (LDA, Bu-Li, t-BuOK, InCl2, AcOAc, Eu(hfc)3) for the transformation into target compounds.
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Reagents | Conditions | Products |
---|---|---|
Dry gaseous NH3, −10 °C, EtOAC:EtOH (1:1) | ||
Dry acetonitrile, N2, reflux, 1 h | ||
CH3NH2, −10 °C, EtOAC:EtOH (1:1) |
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Ivanova, E.; Osipova, M.; Vasilieva, T.; Eremkin, A.; Markova, S.; Zazhivihina, E.; Smirnova, S.; Mitrasov, Y.; Nasakin, O. 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. Int. J. Mol. Sci. 2023, 24, 17196. https://doi.org/10.3390/ijms242417196
Ivanova E, Osipova M, Vasilieva T, Eremkin A, Markova S, Zazhivihina E, Smirnova S, Mitrasov Y, Nasakin O. 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. International Journal of Molecular Sciences. 2023; 24(24):17196. https://doi.org/10.3390/ijms242417196
Chicago/Turabian StyleIvanova, Elizaveta, Margarita Osipova, Tatyana Vasilieva, Alexey Eremkin, Svetlana Markova, Ekaterina Zazhivihina, Svetlana Smirnova, Yurii Mitrasov, and Oleg Nasakin. 2023. "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" International Journal of Molecular Sciences 24, no. 24: 17196. https://doi.org/10.3390/ijms242417196