Synthetic routes towards tetrazolium and triazolium dinitromethylides

Katritzky, Alan R.; Sommen, Geoffroy L.; Gromova, Anna V.; Witek, Rachel M.; Steel, Peter J.; Damavarapu, Reddy

doi:10.1007/s10593-005-0116-5

Cited by 44 publications

(30 citation statements)

References 18 publications

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“…The latter observation led to the conclusion that water was involved in a stage that limited the hydrolysis rate. Further analysis of the results indicated that two mechanisms of the hydrolysis with observed rate constants k 1 ] was proposed. According to the proposal the active complex decomposed rapidly into nitroimidazole 7, nitric(V) acid, and water.…”

Section: -Denitration Of Dinitroimidazoles 1-4mentioning

confidence: 99%

“…48 The products served as starting materials in syntheses of adenines. Two other compounds, the (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) N)adenine and (1-3 H)ribose, were also prepared. The compounds were then enzymatically coupled to isotopically modified ribosyl groups to give respectively substituted adenosines (31, Figure 5).…”

Section: Nucleophilic Cine-substitutionmentioning

confidence: 99%

“…N)imidazol-1′-yl]acetic acid was obtained. The latter acid with bromine and phosphorus trichloride in anhydrous benzene formed a product that was subjected to hydrolysis to afford 2-methyl-4(5)-nitro-1H- (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) N)imidazole in 40% yield. Starting compound 2 was also treated with ( 15 N)ammonia to produce a mixture of isotopically modified and natural nitrous oxide.…”

Section: 32mentioning

confidence: 99%

“…[1][2][3] They are also very valuable to the pharmaceutical chemistry as nitrocontaining synthetic intermediates and drugs. 1,[4][5][6] The potential use of dinitroimidazoles in preparations of new classes of high explosives and antimicrobial drugs has recently focused chemists' interests on 1,4-dinitro-1H-imidazole as the most convenient starting compound in the preparation of several useful products.…”

Section: Introductionmentioning

confidence: 99%

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1,4-Dinitro-1H-imidazoles

Suwiński¹

2015

Arkivoc

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Section: -Denitration Of Dinitroimidazoles 1-4mentioning

confidence: 99%

Section: Nucleophilic Cine-substitutionmentioning

confidence: 99%

Section: 32mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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1,4-Dinitro-1H-imidazoles

Suwiński¹

2015

Arkivoc

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“…5 Its various salts and N-methyl derivatives were prepared from 5-dinitromethyltetrazole (1), 5,6 and the monosodium salt of 1 was also from FOX-7. 7 In the synthesis of tetrazoles containing dinitromethyl moiety, trinitroacetonitrile has been mainly employed. 5,6 Due to easy decomposition, trinitroacetonitrile should be handled with utmost care, and kept in solution.…”

mentioning

confidence: 99%

Synthesis and Characterization of 5-Dinitromethyltetrazole

Lim¹,

Hong²,

Chung

et al. 2008

Bulletin of the Korean Chemical Society

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High‐Density Energetic Mono‐ or Bis(Oxy)‐5‐Nitroiminotetrazoles

Joo

Shreeve

2010

Angewandte Chemie

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Dedicated to Professor Malcolm M. Renfrew on the occasion of his 100th birthdayIn the last decade, the investigation of energetic tetrazolescyanotetrazole, aminotetrazole, azidotetrazole, nitrotetrazole, and nitroiminotetrazole-has led to major developments in the area of high-energetic materials by many research groups. [1] Several exciting classes of 5-substituted tetrazole moieties are introduced in the literature. [2] Tetrazoles can be protonated to form tetrazolium salts [3] or deprotonated to give tetrazolates. [4] While deprotonation increases the thermal stability of tetrazoles, protonation can lower the decomposition temperature. [5] These energetic materials based on high nitrogen content are derived from their high heats of formation due to the large number of NÀN and C À N bonds. [6] The combination of a tetrazole ring with energetic substituent groups containing oxygen atoms, such as nitro groups, nitrate esters, or nitramine, is of interest leading to excellent oxidizers. Current research issues in the field of high energetic materials include increasing oxygen content, which may result in the replacement of ammonium perchlorate in an effort to decrease pollution. Organic 5-nitrotetrazole derivatives, [1k, 7] especially for synthesis of the highly energetic 1-methyl-5-nitrotetrazole, were synthesized in good yields. These were calculated to be endothermic with heats of formation of 2.16 kJ g À1 , which was assessed by means of standard tests and quantum chemical calculations. [7] In addition, the highly energetic, nitrogen-rich 1-methyl-5-nitroiminotetrazole [8] and its salts [8c] can easily be obtained by nitration of aminotetrazole followed by metathesis reactions using silver 1-methyl-5-nitroiminotetrazolate and the guanidinium family of chlorides in aqueous solution with high yields. Although 5-nitroiminotetrazole derivatives and their salts are energetic materials with high nitrogen content, they show good stabilities towards friction and impact, and good thermal stability. [8c, 9] The development of new energetic compounds with similar attractive properties exhibit significant promise in optimizing environmentally benign replacements for toxic materials. [10] In the past few years, the most convenient route to 1substituted 5-aminotetrazole is the addition of amine or hydrazine to cyanogen azide, [11] which was found to be an efficient reagent for the synthesis of readily purified 1-substituted 5-aminotetrazoles from primary amines under non-catalytic mild conditions. Nitration of these aminotetrazoles using 100 % nitric acid has been shown to form mono-, di-, or tri-substituted nitroiminotetrazole derivatives. [12] With these features in mind, our group became interested in examining the analogous chemistry using alkoxy amine derivatives.Here we describe the work leading to a series of nitroiminotetrazole derivatives of oxy nitroiminotetrazoles and their salts, with potentially significant physical and energetic properties. The aim of our study was to elucidate the structures in the crysta...

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Synthetic routes towards tetrazolium and triazolium dinitromethylides

Abstract: probably via dinitromethylide followed by cyclization and loss of nitrogen.

Cited by 44 publications

References 18 publications

1,4-Dinitro-1H-imidazoles

1,4-Dinitro-1H-imidazoles

Synthesis and Characterization of 5-Dinitromethyltetrazole

High‐Density Energetic Mono‐ or Bis(Oxy)‐5‐Nitroiminotetrazoles

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