Synthesis and transformations of picrylacetaldehyde

Vinogradov, V. M.; Далингер, И. Л.; Старосотников, А. М.; Шевелев, С. А.

doi:10.1070/mc2000v010n04abeh001322

Cited by 13 publications

(10 citation statements)

References 4 publications

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“…We found conditions ensuring reaction of I with dimethoxymethyl-(dimethyl)amine (N,N-dimethylformamide dimethyl acetal) to produce enamine IV (Scheme 2 We compared the reactivity of compound I and some nitrotoluenes toward dimethylformamide dimethyl acetal (see table). The results showed that the activity of the 4-methyl group in pyrazole I is most similar to that of the methyl group in 2,4-dinitrotoluene [9].…”

mentioning

confidence: 82%

“…Just the same approach turned out to be successful in the synthesis of benzo-fused heterocycles (benzisoxazoles and indazoles) from 2,4,6-trinitrotoluene [8]. We found conditions ensuring reaction of I with dimethoxymethyl-(dimethyl)amine (N,N-dimethylformamide dimethyl acetal) to produce enamine IV (Scheme 2 We compared the reactivity of compound I and some nitrotoluenes toward dimethylformamide dimethyl acetal (see table).…”

mentioning

confidence: 87%

“…It is known [10] Reactivity of nitrotoluenes and 1,4-dimethyl-3,5-dinitropyrazole (I) toward dimethoxymethyl(dimethyl)amine with published data [8], the reaction involves intermediate formation of pyrazolo [4,3-d]isoxazole VII which undergoes deformylation and opening of the isoxazole ring by the action of a base. The position of the hydroxy group in the pyrazole ring of VIII was determined by the HMBC two-dimensional correlation technique, on the basis of long-range 1 H-13 C coupling constants.…”

mentioning

confidence: 95%

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Nitropyrazoles: XII. Transformations of the 4-Methyl Group in 1,4-Dimethyl-3,5-dinitropyrazole and Cyclization of the Transformation Products

et al. 2005

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A preparative procedure for the synthesis of 1,4-dimethyl-3,5-dinitropyrazole by nitration of 1,4-dimethylpyrazole was developed. The reaction of 1,4-dimethyl-3,5-dinitropyrazole with dimethoxymethyl-(dimethyl)amine (N,N-dimethylformamide dimethyl acetal) gave (E)-N,N-dimethyl-2-(1-methyl-3,5-dinitropyrazol-4-yl)ethenylamine. Acid hydrolysis of the latter afforded (1-methyl-3,5-dinitropyrazol-4-yl)acetaldehyde, and the reaction with sodium nitrite in hydrochloric acid led to formation of 2-hydroxymino-2-(1-methyl-3,5-dinitropyrazol-4-yl)acetaldehyde. The corresponding O-methyloxime and phenylhydrazone reacted with K 2 CO 3 to give 6-methyl-4-nitropyrazolo[4,3-d]isoxazole-3-carbaldehyde O-methyloxime and 1-methyl-3-nitro-4-(2-phenyl-2H-1,2,3-triazol-4-yl)pyrazol-5-ol, respectively. Treatment of (1-methyl-3,5-dinitropyrazol-4-yl)-acetaldehyde with benzenediazonium chloride gave (1-methyl-3,5-dinitropyrazol-4-yl)acetaldehyde phenylhydrazone which underwent intramolecular cyclization with replacement of the 5-nitro group by the action of K 2 CO 3 in acetonitrile; in the reaction with K 2 CO 3 in ethanol, the 5-nitro group was replaced by ethoxy.* For communication XI, see [1].

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confidence: 82%

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confidence: 87%

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confidence: 95%

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Nitropyrazoles: XII. Transformations of the 4-Methyl Group in 1,4-Dimethyl-3,5-dinitropyrazole and Cyclization of the Transformation Products

et al. 2005

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“…Here the reaction is likely to proceed via a 4,6-dinitro-3-formylbenzo[d]isoxazole formation step with subsequent simultaneous decarbonylation and isoxazole cycle opening. 23 The formyl group protection in oxime 64 with the formation of respective acetal, hydrazones, О-methyloxime, and N-phenylamine allows implementing intramolecular nucleophilic substitution of the nitro group resulting in stable benzo [d]isoxazoles: 3-R-4,6-dinitrobenzo[d]isoxazoles 68 are formed on treatment of oximes 67 with K 2 CO 3 in EtOH. Isoxazoles 68 can be prepared directly from oxime 64 without isolating the intermediates.…”

Section: Synthesis Of Benzannelated Five-membered Heterocycles With Tmentioning

confidence: 99%

“…Of note are mild conditions of the TNT reaction with DMF DMA (in toluene at 20 о С). 23 A synthesis of 2,4,6-trinitrophenylacetaldehyde 14 was designed on the basis of enamine 13. 23 This compound is a convenient synthon for the annelating of additional heterocyclic moieties.…”

Section: Reactions Of the Tnt Methyl Groupmentioning

confidence: 99%

Synthesis of benzannelated five-membered heteroaromatic compounds from 2,4,6-trinitrotoluene

Bastrakov¹,

Старосотников²,

Шевелев

2008

Arkivoc

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Methods for the synthesis of five-membered benzannelated heterocyclic compounds from the military explosive 2,4,6-trinitrotoluene (TNT) are summarised. The general approach concerns the transformation of the TNT methyl group followed by either intramolecular substitution of the ortho-nitro group or regioselective substitution of the ortho-nitro group by an appropriate nucleophile and subsequent cyclization.

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Synthesis and characterization of poly(vinyl 2,4,6‐trinitrophenylacetal) as a new energetic binder

Jin

Dong

Peng

et al. 2011

J of Applied Polymer Sci

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Poly(vinyl alcohol) was modified by an aldehyde acetal reaction with 2,4,6-trinitrophenylacetaldehyde to give a new energetic polymer poly(vinyl 2,4,6-trinitrophenylacetal) (PVTNP). The structure of PVTNP was characterized by elemental analysis, ultraviolet-visible spectroscopy, Fourier transform infrared spectroscopy, and nuclear magnetic resonance spectra. The glass-transition temperature of PVTNP was evaluated by differential scanning calorimetry (DSC), and the thermal stability of PVTNP was tested by differential thermal analysis (DTA) and thermogravimetric analysis (TGA). DSC traces showed that the PVTNP polymer had one single glass-transition temperature at 105.3 C. DTA and TGA curves showed that the thermooxidative degradation of PVTNP in air was a three-step reaction, and the percentage of degraded PVTNP reached nearly 100% at 650 C.

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Synthesis and transformations of picrylacetaldehyde

Cited by 13 publications

References 4 publications

Nitropyrazoles: XII. Transformations of the 4-Methyl Group in 1,4-Dimethyl-3,5-dinitropyrazole and Cyclization of the Transformation Products

Nitropyrazoles: XII. Transformations of the 4-Methyl Group in 1,4-Dimethyl-3,5-dinitropyrazole and Cyclization of the Transformation Products

Synthesis of benzannelated five-membered heteroaromatic compounds from 2,4,6-trinitrotoluene

Synthesis and characterization of poly(vinyl 2,4,6‐trinitrophenylacetal) as a new energetic binder

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