Application of Primary Allylamines from Morita–Baylis–Hillman Adducts: Cyanogen Azide Mediated Synthesis of Substituted 5‐Aminotetrazoles and Their Attempted Transformation into Tetrazolo[1,5‐<i>a</i>]pyrimidinones

Nag, Somnath; Bhowmik, Subhendu; Gauniyal, Harsh M.; Batra, Sanjay

doi:10.1002/ejoc.201000586

Cited by 20 publications

(5 citation statements)

References 56 publications

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“…Pharmaceutical applications of tetrazoles include antiallergic, antimicrobial, sedatives [5], anti-inflammatory [6], anti-HIV [7], hormonal [8], lipophilic spacers [9] and diuretics activity [10]. Furthermore, a range of proline derived tetrazoles have been reported as an enantioselective catalyst in asymmetric synthesis; additionally, they play a very important role as ligands in coordination chemistry [11].…”

Section: Introductionmentioning

confidence: 99%

Ultrasound-promoted one-pot three component synthesis of tetrazoles catalyzed by zinc sulfide nanoparticles as a recyclable heterogeneous catalyst

Naeimi

Kiani

2015

Ultrasonics Sonochemistry

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Ultrasound irradiation was applied for the appropriate and rapid synthesis of 1-substituted tetrazoles through cyclization reaction of various primary amines, sodium azide and triethyl orthoformate. This reaction was effectively catalyzed by ZnS nanoparticles as an efficient, recoverable and reusable catalyst. Compared with conventional methods, this method has the considerable advantages such as shorter reaction times, easier work-up, purer products with high yields and mild conditions. The ZnS nanoparticles catalyst is an excellent instance to replace Brønsted acids for the preparation of 1-substituted tetrazole derivatives in very short reaction times with excellent yields. The catalyst can be recovered and reused several times without significant loss of its catalytic activity.

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Section: Introductionmentioning

confidence: 99%

Ultrasound-promoted one-pot three component synthesis of tetrazoles catalyzed by zinc sulfide nanoparticles as a recyclable heterogeneous catalyst

Naeimi

Kiani

2015

Ultrasonics Sonochemistry

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“…Although several methods for the synthesis of 5-aminotetrazoles have been reported, the methods suffer from several drawbacks. For example, hydrazoic acid is a highly toxic reagent; 22 cyanogen bromide on contact with water or water vapour will emit toxic, flammable, corrosive hydrogen bromide and hydrogen cyanide; [23][24][25] use of heavy metal salts (Hg or Pb) may have serious environmental impacts; 26 and Zr is an expensive reagent. 27 Moreover, the tandem procedure, with thiocyanogen as starting material and using ammonia, sodium azide, iodine and triethylamine, results in the production of 5-aminotetrazole in quite low yield (only 10%).…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of 1-(4-Bromophenyl)-1H-Tetrazol-5-Amine and Related Amide Derivatives

Yang

Ouyang

Sun

et al. 2017

Journal of Chemical Research

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An efficient one-pot synthesis of 1-(4-bromophenyl)-1 H-tetrazol-5-amine was performed using 4-bromoaniline as the starting material. A novel and widely applicable amidation procedure was then employed, whereby 1-(4-bromophenyl)-1 H-tetrazol-5-amine was acylated with different acyl chlorides in the presence of lithium bis(trimethylsilyl)amide as catalyst, for the high-yield synthesis of [1-(4-bromophenyl)-1 H-tetrazol-5-yl]amide derivatives.

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“…In addition, because a higher percentage of the decomposition products is dinitrogen, these energetic ionic salts except perchlorate are more environmentally acceptable. ,,, Azoles, the five-membered nitrogen-containing heterocycles, are excellent ions for energetic salts. A large number of azole-based energetic salts have been synthesized and investigated, − especially the 1,2,4-triazole series. − Among them, 3-azido-1,2,4-triazole has been used as a precursor to some energetic materials, in part due to its dual acid and base nature . It is a strong enough base to form perchlorate and nitrate salts …”

Section: Introductionmentioning

confidence: 99%

First-Principle Studies on the Pressure-Induced Structural Changes in Energetic Ionic Salt 3-Azido-1,2,4-triazolium Nitrate Crystal

et al. 2012

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Periodic first-principle calculations have been performed to study the effect of high pressure on the geometrical and electronic structures of the energetic ionic salt 3-azido-1,2,4-triazolium nitrate (ATAN) under hydrostatic pressure of 0–300 GPa. The local density approximation with CA-PZ functional has been adopted because the crystal structure optimized with it agrees better with the experimental results than with other functionals at the ambient pressure. When the hydrostatic compression is exerted upon the ATAN crystal, the unit cell parameters, density, total energy, interatomic distances, bond angles, atom charges, bond populations, band structure, and density of states of ATAN crystal change regularly with the increase in pressure except at 200 GPa where the structural transformations occur. Although the azido group bends gradually and slowly to form a five-membered tetrazole ring, the H atom in the adjacent cation transfer to the terminal N atom of the azido group and a new covalent bond forms at 200 GPa; thus, the azide–tetrazole ring–chain transformation has not completely been realized even under the higher pressure owing to this new covalent bond.

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Application of Primary Allylamines from Morita–Baylis–Hillman Adducts: Cyanogen Azide Mediated Synthesis of Substituted 5‐Aminotetrazoles and Their Attempted Transformation into Tetrazolo[1,5‐a]pyrimidinones

Cited by 20 publications

References 56 publications

Ultrasound-promoted one-pot three component synthesis of tetrazoles catalyzed by zinc sulfide nanoparticles as a recyclable heterogeneous catalyst

Ultrasound-promoted one-pot three component synthesis of tetrazoles catalyzed by zinc sulfide nanoparticles as a recyclable heterogeneous catalyst

Facile Synthesis of 1-(4-Bromophenyl)-1H-Tetrazol-5-Amine and Related Amide Derivatives

First-Principle Studies on the Pressure-Induced Structural Changes in Energetic Ionic Salt 3-Azido-1,2,4-triazolium Nitrate Crystal

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