The preparation of 2,6‐diaminopyrazine, 2,6‐diazidopyrazine and some of their derivatives

Shaw, John T.; Brotherton, Christine E.; Moon, Robert W.; Winland, Mark D.; Anderson, Mark; Kyler, Keith S.

doi:10.1002/jhet.5570170103

Cited by 14 publications

(4 citation statements)

References 12 publications

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“…Compound 2,6-diazidopyrazine ( 2 ) was synthesized from a readily available starting material, 2,6-dichloropyrazine ( 1 ), using a previously established method with slight modifications . Compound 2 was treated with a blend of 100% HNO 3 and concentrated H 2 SO 4 at room temperature (25 °C) for 6 h anticipating the formation of 3,5-diazido-2-nitropyrazine, 2,6-diazido-3,5-dinitropyrazine and 5-nitro-[1,2,5]oxadiazolo[3,4- e ]tetrazolo[1,5- a ]pyrazine 3-oxide or their mixtures.…”

Section: Resultsmentioning

confidence: 99%

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Exploring the Explosive Potential: Synthesis and Characterization of Ring-Fused Oxadiazolo[3,4-b]pyrazine 1-Oxide Polymorphs with Balanced Energetic Properties

Yadav,

Devi,

Ghule

et al. 2024

Org. Lett.

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A novel fused-ring compound, 5-azido-6-oxo-6,7-dihydro-[1,2,5]oxadiazolo [3,4-b]pyrazine 1-oxide (3a), was synthesized for the first time with simple two-step process and characterized using various spectroscopic techniques such NMR, IR, EA and HRMS. Two polymorphs (α-3a and β-3a) identified by SCXRD differ in crystal packing and noncovalent interactions, demonstrating high density, substantial heat of formation, and superior detonation properties with reduced mechanical sensitivity compared to TNT, TATB, and close to RDX, suggesting their potential as environmentally friendly high energy density materials.

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Section: Resultsmentioning

confidence: 99%

“…Compound 2,6-diazidopyrazine (2) was synthesized from a readily available starting material, 2,6-dichloropyrazine (1), using a previously established method with slight modifications. 35…”

Section: Synthesismentioning

confidence: 99%

Exploring the Explosive Potential: Synthesis and Characterization of Ring-Fused Oxadiazolo[3,4-b]pyrazine 1-Oxide Polymorphs with Balanced Energetic Properties

Yadav,

Devi,

Ghule

et al. 2024

Org. Lett.

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“…2,6-Diaminopyrazine (5) 7 (Scheme 2) prepared in two steps from 2,6-dichloropyrazine, 8 was treated with N-bromosuccinimide to give 2,6-diamino-3,5-dibromo-1,4pyrazine (6) in moderate overall yield; in our hands, this method was more efficient than the synthesis of Y. C. Tong starting from tetrabromopyrazine. 9 The following step was a double Suzuki coupling reaction 10,11 with phenylboronic acid and 4-methoxyphenylboronic acid to yield respectively the 3,5-diaryl-2,6-diaminopyrazines 7a and 7b.…”

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confidence: 80%

2,6-Diamino-3,5-diaryl-1,4-pyrazine Derivatives as Novel Antioxidants

Cavalier¹,

Burton²,

Tollenaere³

et al. 2001

Synthesis

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The coupling of arylboronic acids with 2,6-diamino-3,5-dibromo-1,4-pyrazine (6) gave 2,6-diamino-3,5-diaryl-1,4-pyrazines (7). The reaction of 7 with methyl glyoxal in aqueous EtOHHCl led to the N,N'-disubstituted products 8, instead of the expected bicyclic imidazolopyrazinones 1. The 2,6-bis[1-(ethoxycarbonyl)-ethylamino]-3,5-diaryl-1,4-pyrazines 8 are powerful inhibitors of the AAPH-induced linoleate peroxidation.Recently we became interested in the synthesis of imidazolopyrazinone derivatives 1 (Scheme 1) as potential antioxidants useful in medicinal chemistry for the design of drugs against injuries caused by oxidative stress. 1,2 Coelenterazine (CLZ), a naturally occurring imidazolopyrazinone of marine origin (1: R 1 = p-HO-Ph; R 2 = PhCH 2 ; R 3 = p-HO-PhCH 2 ; R 4 = H), is the luminescent substrate of enzymes (luciferases) producing light in the presence of oxygen. 3 Synthetic derivatives of coelenterazine can be obtained by condensing 2-amino-1,4-pyrazine precursors 2 with a-keto-aldehydes 3 (or the corresponding acetals) in aqueous acidic medium (Scheme 1). 4 Two routes have been exploited for the synthesis of aminopyrazines 2 equipped with natural or non-natural substituents R 1 , R 2 , and R 4 : (i) condensation of 1,2-propanedione-2-oxime derivatives with 2-amino-propionitrile compounds to form the substituted heterocycles; 5 (ii) functionalization of bromo-aminopyrazine derivatives via a Suzuki coupling reaction with boronic acid derivatives. 6 This last method was exemplified in our group for the preparation of a series of 3,5-diaryl-2-amino-1,4-pyrazines 2 (R 4 = H) and the related 6,8-diaryl-imidazolopyrazinones 1 (R 1 and R 2 = aryl; R 4 = H) which reveal to be powerful antioxidants. 1b

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“…To synthesize LLM-105, Bellamy − used 2,6-diaminopyrazine as the starting material to obtain the target product LLM-105 through a two-step process of oxidation and nitration. However, the side product of oxidation in this method has properties similar to those of the main product, which is not conducive to separation and purification, and the nitration reaction process is difficult to control.…”

Section: Introductionmentioning

confidence: 99%

Thermal Risk Analysis Based on Reaction Mechanism: Application to the 2,6-Diaminopyrazine-1-oxide Synthesis Process

Wang

Liao

et al. 2021

Org. Process Res. Dev.

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Thermal risk analysis is essential for the development of chemical reactions. This work should be carried out on the basis of a thorough comprehension of the reaction mechanism. In this article, the synthesis process for 2,6-diaminopyrazine-1-oxide (DAPO), an important intermediate in the synthesis of the famous explosive 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105), was employed to show the importance of understanding the reaction mechanism for thermal risk analysis. First, we investigated the reaction mechanism of DAPO synthesis. The reaction mechanism was divided into two stages on the basis of the amount of triethylamine dosed: the first half of triethylamine dosing and the second half of triethylamine dosing until the end of the reaction. Then the thermal properties of DAPO synthesis and the thermal stability of the materials involved were experimentally studied using a reaction calorimeter (RC1) and a differential scanning calorimeter (DSC), respectively. The results show that the temperature corresponding to the maximum reaction rate reached in a time of 24 h under adiabatic conditions (T D24) is higher than the maximum temperature of the synthesis reaction (MTSR) for both of these stages, indicating that once cooling failure occurs, immediately stopping addition of triethylamine could prevent the occurrence of secondary decomposition.

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The preparation of 2,6‐diaminopyrazine, 2,6‐diazidopyrazine and some of their derivatives

Cited by 14 publications

References 12 publications

Exploring the Explosive Potential: Synthesis and Characterization of Ring-Fused Oxadiazolo[3,4-b]pyrazine 1-Oxide Polymorphs with Balanced Energetic Properties

Exploring the Explosive Potential: Synthesis and Characterization of Ring-Fused Oxadiazolo[3,4-b]pyrazine 1-Oxide Polymorphs with Balanced Energetic Properties

2,6-Diamino-3,5-diaryl-1,4-pyrazine Derivatives as Novel Antioxidants

Thermal Risk Analysis Based on Reaction Mechanism: Application to the 2,6-Diaminopyrazine-1-oxide Synthesis Process

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