Nitroacetonitrile as a versatile precursor in energetic materials synthesis

Abstract

Nitroacetonitrile is a useful synthetic precursor capable of participating in a wide range of reactions and enables the simple synthesis of annulated heterocyclic systems which are rapidly becoming promising new energetic materials.

Methods of Synthesis and Antiviral Activity of New 4-Alkyl-3-Nitro-1,4-Dihydroazolo[5,1-c][1,2,4]Triazin-4-ols

“…IR spectra were recorded on a Bruker Alpha spectrometer equipped with a ZnSe ATR accessory. 1 Н, 13 C, and 19 F NMR spectra were recorded on a Bruker Avance NEO 600 instrument (600, 151, and 565 MHz, respectively) for samples in CD 3 CN and Me 2 CO-d 6 solutions, with TMS used as internal standard. Elemental analyses were performed on a PerkinElmer 2400 Series II CHNS elemental analyzer.…”

“…13 C NMR spectrum (СD 3 СN), δ, ppm (J, Hz): 8.6; 31.3; 88.8; 120.1 (q, J = 270.3); 143.8; 148.7; 153.9 (q, J = 39.3). 19 F NMR spectrum (СD 3 СN), δ, ppm: -67.13 (CF 3 ). Found, %: С 29.91; H 2.48; N 30.00.…”

“…The complete X-ray diffraction analysis dataset for compound 8j was deposited at the Cambridge Crystallographic Data Center (deposit CCDC 2042591). Supplementary information file containing 1 Н, 13 C, and 19 F NMR spectra of the synthesized compounds is available at the journal website at http://link.springer.com/ journal/10593.…”

“…16 Nitro synthons have been of particular interest in the synthesis of azolo [1,2,4]triazines. Suitable nitro components that have been used in these syntheses are ethyl nitroacetate, 9 ethyl nitromalonate, 17 nitroacetonitrile, [18][19][20] nitromalonic aldehyde, 17 and nitroacetaldehyde in the form of its potassium salt. 21 Promising synthetic building blocks for the assembly of triazine ring include α-nitro ketones, which are highly reactive compounds with a broad synthetic potential but low thermodynamic stability, which is a drawback for their synthetic applications.…”

C–H Amination of Nitro Azaheterocyclic Compounds by Vicarious Nucleophilic Substitution

“…1 Similarly, the nitro aza-heterocycles primary amines appear in a wide range of applications in the preparation of various functional heteroarenes, especially in the synthesis of some energetic materials. 2 As such, the amination of nitro azaheterocyclic compounds is highly sought-after in organic synthesis. In the past few years, some methods for the amination of arenes or heteroarenes have been reported and include the nitration/reduction, 3 transition-metal catalyzed cross-coupling, 4 and arene C-H amination (Fig.…”