Guanidine Nitrate Research Articles

Ethoxyphathalimide linked some 2, 4, 8-Triphenyl-4H-9-thia-1, 4a, 5, 7-tetraaza-fluoren-6-ylamine derivatives: Synthesis and Pharmacological Evaluation from Chalcone

Synthesis of benzalacetophenones (1a-c) has been achieved by the aldol condensation of substituted acetophenone with benzaldehyde. These were treated with thiourea by utilizing HCl to give substituted dihydropyrimidine-thiones (2a-c). Cyclization of these compounds with DMF and chloroacetic acid yielded pyrimidothiazolidinone moieties (3a-c). Reaction of benzaldehyde with 3a-c produced corresponding chalcone derivatives (4a-c). These chalcone derivatives when treated with guanidine nitrate in presence of a base gave (5a-c). Condensation of 5a-c with bromoethoxyphthalimide afforded titled compounds (6a-c). Structures of prepared scaffolds were established by the spectral studies, elemental analysis and chemical tests. Subsequently, heterocyclic hybrids (5a-c, 6a-c) were assayed to their in vitro anti-microbial activity against a variety of infectious strains of bacteria and fungi.

Degradation of guanidine nitrate upon exposure to nitrogen oxide gases

Degradation of guanidine nitrate upon exposure to nitrogen oxide gases

Synthesis of Novel Oxo Pyrimido Pyrimidine and Their Derivatives

Abstract: Pyrimidine derivatives are synthesized to possess various pharmacological and biological activities. In the present work, we have synthesized 3-(4-methoxyphenyl)-1-phenyl prop-2-en-1-one (1) (chalcone) by using 4-methoxybenzaldehyde and acetophenone in the presence of alcoholic KOH by Claisen-Schmidt condensation reaction. After purification and characterization by physical and spectral methods, The synthesized chalcone have been converted into 6-(4-methoxyphenyl)-4- phenyl-1,6-dihydropyrimidin-2-amine (2) by treating with guanidine nitrate in the presence of alcoholic KOH. The structure (2) has been characterized by spectral analysis. The synthesized compound (2) is further reacted with ethyl 2-cyano-3, 3-bis (methylthio)acrylate in the presence of catalytic amount of potassium carbonate in DMF under reflux condition to givenovel 2- (4-methoxyphenyl)-8-(methylthio)-6-oxo-4-phenyl-1,6,9,9a-tetrahydro-2H-pyrimido[1,2-a] pyrimidine-7-carbonitrile(3) in good yields. The compound (3) possesses replaceable methylthio (-SCH3) group at 8 position. The compound (3) is further reacted with various nucleophiles like substituted aromatic amines, aromatic phenols, hetryl amines and active methylene compounds to give 2-(4-methoxyphenyl)-8-substituted-6-oxo-4-phenyl-1,6,9,9a-tetrahydro-2H-pyrimido[1,2-a]pyrimidine-7-carbonitrile in good yields.

Synthesis of some ethoxyphthalimide derivatives of pyrazoloisoxazoles and pyrazolopyrimidines and their antimicrobial and anticancer screening

Synthesis of 4-arylidene-5-methyl-2,4-dihydro-3 H -pyrazol-3-one ( IIIa-d ) has been achieved by the condensation reaction between 5-methyl-2,4-dihydro-3 H -pyrazol-3-one ( I ) and 4-substituted benzaldehydes ( IIa-d ). Ethyl acetoacetate and hydrazine hydrate in absolute alcohol undergo cyclization reaction to give ( I ). 4-Arylidene-5-methyl-2,4-dihydro-3 H -pyrazol-3-ones ( IIIa-d ) have been converted to corresponding ethoxyphthalimide derivatives ( IVa-d ) by treatment with phthalimidoxyethyl bromide ( A ). 1-N-Ethoxyphthalimido-3-methyl-4-(4-substituted benzylidene) pyrazol-5-one ( IVa-d ) has been reacted with hydroxylamine hydrochloride and guanidine nitrate separately to yield ethoxyphthalimide substituted pyrazolo[3,4-c]isoxazoles ( Va-d ) and pyrazolo[3,4-d]pyrimidines ( VIa-d ) respectively. All the compounds have been characterized by elemental and spectral analysis mainly IR, 1 H NMR and mass spectroscopy. Synthesized compounds have also been screened for various biological activities viz. antibacterial, antifungal, antiviral and anticancer.

Acid-Free Copper-Catalyzed Electrophilic Nitration of Electron-Rich Arenes with Guanidine Nitrate.

A practical copper-catalyzed nitration of electron-rich arenes with trimethylsilyl chloride and guanidine nitrate is reported. A variety of nitrated products were generated in moderate to excellent yields (32-99%) at ambient temperature under acid-free, open-flask, and operationally simple conditions.

Effects of Ozone on the thermal decomposition behavior of Guanidine Nitrate

Effects of Ozone on the thermal decomposition behavior of Guanidine Nitrate

Divalent nitrogen-rich cationic salts with great gas production capacities

Monocyclic nitrogen-rich 3-(aminomethyl)-4,5-diamine-1,2,4-triazole (1) and fused cyclic 3,7-diamine-6-(aminomethyl)-[1,2,4] triazolo [4,3-b] [1,2,4] triazole (9) were synthesized through the convenient cyclization reaction from the readily available reactant. Their energetic salts with high nitrogen content were proved to be rare examples of divalent monocyclic/fused cyclic cationic salts according to the single crystal analyses. The structure of intermediate B was also identified and verified by its trivalent cation crystal 17.5H2O indirectly. Energetic compounds 2–8 and 10–17 were fully characterized by NMR spectroscopy, infrared spectroscopy, differential scanning calorimetry, elemental analysis. These energetic salts exhibit good thermal stability with decomposition temperatures ranged from 182 °C to 245 °C. The sensitivity of compounds 2, 6, 10 and 14 is similar or superior to that of RDX while the others were much more insensitive to mechanical stimulate. Furthermore, detonation velocity of 10 (8843 m/s) surpass that of RDX (D = 8795 m/s). Considering the high gas production volume (≥808 L/kg) of 2, 4, 10 and 12, constant-volume combustion experiments were conduct to evaluate their gas production capacities specifically. These compounds possess much higher maximum gas-production pressures (Pmax: 7.88–10.08 MPa) than the commonly used reagent guanidine nitrate (GN: Pmax = 4.20 MPa), which indicate their strong gas production capacity.

Green synthesis, characterization, biological evaluation and docking study of some pyrazoline and pyrimidine derivatives

Green and classical techniques have been utilized for preparing of a variety of aryl - substituted pyrazoline and pyrimidine derivatives (2-8). Reactions of chalcones 1 with semicarbazide and thiosemicarbazide, nicotinic acid hydrazide and amino guanidine hydrochloride afforded the corresponding N-substituted pyrazoline derivatives 2-5. Pyrimidine derivatives 6-8 were achieved via reaction of chalcone derivatives 1 with several reagents namely: guanidine nitrate, thiourea and 6-amino-2-thioxo-2,3- dihydropyrimidin-4(1H)-one under conventional and ultrasonic conditions. Ultrasonic method was found to be an easy work-up procedure and it gave high yield in comparison with conventional method. The structures of new synthesis compounds were characterized by elemental and spectral analyses. Some of newly compounds were tested in vitro antibacterial activity against some gram–positive and gram–negative. The antimicrobial results displayed favorable antimicrobial activity. Molecular docking has been perfomed for compound 5b using MOE 2008.10, The data results obtained are quite promising.

Quinoline and 2-nitroimino-1, 3-diazacycloalkane hybrids: Design, synthesis and insecticidal activity

A library of new hybrid molecules comprising quinoline, 2-nitroimino-1, 3-diazacycloalkane motifs were designed and synthesized as plausible neonicotinoid analogues. These compounds were synthesized from 2-chloro/aryloxy-3-formyl quinolines and guanidine nitrate with the coupling of 2-chloro/aryloxy-3-(chloromethyl)quinolines, 2-nitroimino-1, 3-diazacycloalkanes under phase transfer catalysis (PTC) as crucial step. All the compounds were obtained in excellent yields (80–90%) and were characterized by 1H, 13C NMR and mass spectrometry. The newly generated compounds were screened for insecticidal activity against aphids in safflower field and some of them displayed moderate activity.

Construction of a Novel Barium‐Free Green‐Light Emitting Illuminant Based on Boron Carbide

AbstractGreen‐light emitting illuminant and green pearls that are currently being used for pyrotechnics are mainly composed of barium carbonate and polyvinyl chloride (PVC), which lead inevitably to the substantial generation of abundant harmful products for environmental pollution. There is thus considerable scope for the development of a novel emitting illuminant with an improved “green” composition instead of compositions incorporating barium based oxidants and polyvinyl chloride for environmental protection. For this purpose, a new composition composed of boron carbide, potassium perchlorate, and guanidine nitrate with a suitable burning rate of 5∼15 mm/s required for fireworks, the high luminous intensity of 34665 Cd and spectral purity of 67.1 % at a primary wavelength of 562 nm was developed. Notably, PM10 data demonstrated that the new composition generated less than half the amount of the smoke relative to the original one. More importantly, all of the safety parameters of this new formulation meet well with the standards’ requirements, i. e., a remarkable low sensitivity to friction (0 %) and impact (8 %), relative stability to electric discharge (374.4 mJ), flame (14.0 cm) and heating (unburned, unexploded at 75 °C for 48 h), as well as a high ignition temperature of 504.0 °C and a low moisture absorption rate (0.66 %). Taken together, the new emitting illuminant developed herein showed great potential to be used for fireworks and signal flare in both military and civilian applications.

CuO Nanocatalyzed Improved Synthesis of Some 2- Aminopyrimidines

An effective and simple method for the synthesis of substituted 2- aminopyrimidines has been developed using chalcones, guanidine nitrate and aqueous sodium hydroxide in the presence of CuO nanoparticle as catalyst. The developed strategy has various advantages such as short reaction time, improved yields and the catalyst used is recyclable and inexpensive. DOI: http://dx.doi.org/10.17807/orbital.v13i3.1621

Burning Rate Characterization of Guanidine Nitrate and Basic Copper Nitrate Gas Generants with Metal Oxide Additives

ABSTRACT Automotive airbag gas generants have been studied extensively to meet design and safety requirements. Additives have historically been used to increase their burning rates, but the effects of additive size have not been thoroughly investigated. The current study evaluated the effects of nano- and micro-sized metal oxides on the combustion of guanidine nitrate (GN) and basic copper nitrate (BCN) gas generant systems. Three metal oxide additives were chosen for this study: alumina (Al2O3), ceria (CeO2), and titania (TiO2). Nano- and micro-sized particles were incorporated into gas generants at a mass loading of 4%. Cylindrical pellets with and without additive particles were manufactured, and their homogeneity was confirmed through scanning electron microscopy analyses. Pellets were burned over a range of pressures from 6.9 MPa (1,000 psi) to 27.6 MPa (4,000 psi). Micro-ceria was the only additive observed to enhance the burning rate relative to the baseline.

Pyrrole-Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles.

An efficient method for the synthesis of pharmaceutically prospective pyrrole–aminopyrimidine ensembles (in up to 91% yield) by the cyclocondensation of easily available acylethynylpyrroles with guanidine nitrate has been developed. The reaction proceeds under heating (110–115 °C, 4 h) in the KOH/DMSO system. In the case of 2-benzoylethynylpyrrole, the unexpected addition of the formed pyrrole–aminopyrimidine as N- (NH moiety of the pyrrole ring) and C- (CH of aminopyrimidine) nucleophiles to the triple bond is observed.

MCF-7 Human Breast Adenocarcinoma Anticancer and Antimicrobial, in silico Docking and ADME Prediction Studies of Furan Moiety Containing Substituted 2-Aminopyrimidine Derivatives

A series of 4(5-(4-chlorophenyl)furan-2-yl)-6-phenylpyrimidin-2-amine derivatives (5a-h) were synthesized from 2-(4-chlorophenyl)-5-styrylfuran (3a-h) with guanidine nitrate in absolute ethanol under conventional method and evaluated for their in vitro anticancer, antimicrobial activities and in silico studies. The chemical structure of the furan moiety containing substituted amino pyrimidine derivatives (5a-h) were elucidated from spectroscopic analysis like infrared, 1H & 13C NMR spectral data and CHN analysis. in silico docking studies were predicted for the synthesized compounds (5a-h) using bacterial protein 1UAG and in silico ADME predictions were also carried for the synthesized compounds (5a-h). The in vitro anticancer study was carried the compound 5b by MMT assay. Compound 5b shows the LC50 value of 120.15 ± 0.003 μg/mL. in vitro Antimicrobial activities were screened for the compounds (5a-h) using different strains. Compound 5h has electron withdrawing group in benzene ring substituted in the para position showed good antimicrobial activity against all the bacterial strains and fungal strains. in silico studies, compound 5h shows excellent docking score (-9.7 kcal/mol) compared with ciprofloxacin (-7.8 kcal/mol).

Tricyclic nitrogen-rich cation salts based on 1,2,3-triazole: Chemically stable and insensitive candidates for novel gas generant

A new tricyclic nitrogen-rich compound 4,5-bis(4,5-diamine-1,2,4-triazole-3-yl)-2H-1,2,3-triazole (2) was synthesized. Monovalent and divalent cations based on 1,2,3-triazole backbone were developed for energetic salts 3–13. It is worth mentioning that energetic salt 8 was obtained as a unique zwitterionic salt. These energetic compounds exhibit good thermal stability and positive heat of formation. Most of these newly synthesized compounds were insensitive to mechanical stimulation (IS ≥ 24 J, FS ≥ 252 N), while the sensitivity of compound 4 (IS = 7 J, FS = 120 N) is similar to that of RDX (IS = 7.4 J, FS = 120 N). Additionally, crystal analysis and theoretical calculations of crystals 2, 3, 4, 8 were carried to explore the relationship between strong hydrogen bonds and physicochemical properties. Furthermore, dinitramide salt 5 and zwitterionic salt 8 have relatively high theoretical detonation properties (5: D = 8770 m s−1, 8: D = 8545 m s−1), which are close to RDX (D = 8795 m s−1). The compounds 2–5, 8 possess outstanding combustion performance (Pmax: 4.57–13.38 MPa) tested by constant-volume combustion experiments, which are superior to frequently-used gas generant guanidine nitrate. All the results demonstrate that dinitramide salt 5 and zwitterionic salt 8 with high volumes of detonation gas (5: 826.74 L kg−1; 8: 799.77 L kg−1), moderate detonation performance and appropriate mechanical sensitivities (5: IS = 28 J, FS > 360 N; 8: IS > 40 J, FS > 360 N) may be useful as novel gas generant.

Synthesis Optimization of Guanidinium Dinitramide (GDN).

Dinitramide anion [-N(NO₂)₂] salt composed of resonance structure is a plausible oxidizing agents, as efficient propellant. Among them, guanidinium dinitramide (GDN) is an organic compound improving the stability against moisture, as well long term storage. An additional advantage composed guanidinium ion is the reaction efficient via the decomposed by-product during pyrognostics, maximum yield of 99%. The types of GDN (GDN-I, II, III, IV, V) were synthesized using several starting material such as guanidine acetate, chloride, carbonate, nitrate and sulfate under hydrodeprivation. In this work, the intermediates formed in these processes were closely identified and their thermal properties, and chemical structure were examined. The absorption peaks by Fourier transform infrared (FT-IR) were found guanidinium infrared frequencies (3452, 3402, 3354, 3278, 1642 cm-1) and dinitramide infrared frequencies (3208, 1570, 1492, 1416, 1337, 1179, 1000 cm-1). The activation energy of GDN samples were obtained Ea = 53.26 Kcal/mole (GDN-I), 50.94 Kcal/mole (GDN-II), 52.34 Kcal/mole (GDN-III), 62.19 Kcal/mole (GDN-IV), 55.32 Kcal/mole (GDN-V) from exothermic at over 153°C.

Analyses of the thermal characteristics and gaseous products of guanidine nitrate/basic copper nitrate mixtures using calorimetry with high resolution mass spectrometry

This work assessed the pyrolysis of a well-established gas generating agent consisting of a mixture of guanidine nitrate (GN) with basic copper nitrate (BCN), using thermogravimetry-differential scanning calorimetry in conjunction with high resolution mass spectrometry (TG/DSC/HRMS). This instrumentation simultaneously determined mass changes and heat flow, and also permitted evaluation of evolved gases on an accurate mass basis. Fragmentation ratio correction was used to analyze the MS data acquired via electron ionization. GN/BCN mixtures were found to undergo pyrolysis to evolve H2O, N2, NO, CO2 and N2O. Using HRMS, species having similar masses, such as CO2 and N2O, CO and N2, and NH3 and OH, were successfully distinguished. The thermal analysis data and the gas evolution results allowed a pyrolysis mechanism to be proposed. In this mechanism, a copper(II) complex obtained from the BCN catalytically decomposes NH3 generated from the GN to produce N2 and H2O. The pyrolysis of a mixture of GN and BCN thus provides a synergistic effect that increases the heat and gas output.

Nickel(II) Chromite Nanoparticles: An Eco-Friendly and Reusable Catalyst for Synthesis of 2,4-Diamino-6-aryl-pyrimidine-5-yl Cyanides under Ultrasonic Radiation.

One of the principal factors in the field of research in green chemistry is to drive chemical reactions using ultrasonication as a versatile synthetic tool. Moreover, nanostructured metal salts occupy an important position as low cost, efficient, heterogeneous, and green catalysts in chemical reactions. Pyrimidine has also acquired significance because it is a core structure in a variety of natural and non-natural agents, many of which display versatile biological activities and medical applications. The aim of this study was to explore the role of nickel(II) chromite nanoparticles (NiCr2O4 NPs) as a green and recyclable catalyst for the synthesis of 2,4-diamino-6-arylpyrimidine- 5-yl cyanides under ultrasonic radiation. A direct cyclocondensation reaction of guanidine nitrate, aromatic aldehydes, and malononitrile was performed using NiCr2O4 NPs as an effective heterogeneous catalyst under ultrasonic radiation at room temperature conditions to prepare 2,4-diamino-6-aryl-pyrimidine-5-yl cyanides in high yields. The described catalyst was prepared successfully according to a simple hydrothermal route and fully characterized by the X-Ray diffraction (XRD) technique, dispersive energy X-Ray (EDS) analysis, scanning electron microscopy (SEM), and dynamic light scattering (DLS). A number of 2,4-diamino-6-aryl-pyrimidine-5-yl cyanides were effectively synthesized in high yields (94-98%) within short reaction times (15 min). All synthesized compounds were well characterized by IR, 1H and 13C NMR spectroscopy, and also by elemental analyses. In conclusion, a simple, efficient, and green synthesis of 2,4-diamino-6-arylpyrimidine- 5-yl cyanides was developed using NiCr2O4 NPs as a green nanocatalyst, and under ultrasound radiation as a green tool. The mild reaction conditions, avoiding the use of toxic solvents or reagents, high atom economy, high yields, and simple workup are the attractive features of this new protocol.

Aqueous‐Mediated green synthesis of novel spiro[indole‐quinazoline] derivatives using kit‐6 mesoporous silica coated Fe3O4 nanoparticles as catalyst

AbstractIn this work, a series of eight new spiro[3,4′]1,3‐dihydro‐2H‐indol‐2‐one‐2′‐amino‐4′,6′,7′,8′‐tetrahydro‐2′,5’(1’H,3’H)‐quinazoline‐diones were successfully synthesized through a three‐component reaction of 1H‐indole‐2,3‐diones (isatins), guanidine nitrate, and 1,3‐cyclohexanediones, by use of Kit‐6 mesoporous silica coated Fe3O4 nanoparticles (Fe3O4@SiO2@KIT‐6) as a highly efficient magnetically separable nanocatalyst in aqueous media at 60°C. Several notable features of thiseco‐friendly protocol are high yields of products, short reaction times, operational simplicity, and the use of easily available and recyclable catalyst.

Study on the Mechanical Properties of Solid Composite Propellant Used as a Gas Generator

A gas generating propellants are used as initiators of liquid rocket propellants turbopumps and have as desired characteristic a high-volume production of low-temperature gas. In this context, some formulations of composite propellant containing polyurethane (based on liquid hydroxyl-terminated polybutadiene), guanidine nitrate, ammonium perchlorate, and additives were evaluated and characterized in order to verify their potential as gas generator propellant, as well as to evaluate the influence of additives on mechanical properties. The formulations were prepared, analyzed, and tested for mechanical properties.