876716-26-6Relevant articles and documents
The influence of ultrasonic irradiation on catalytic performance of ZnO nanoparticles toward the synthesis of chiral 1-substituted-1H-tetrazolederivatives from α-amino acid ethyl esters
Mohamed, Yasser Mahmoud A.,Attia, Yasser A.
, (2020/05/18)
In this work, a simple and greener protocol for the synthesis of 1-substituted 1H-tetrazole derived from α-amino acid ethyl esters was demonstrated in the presence of zinc oxide nanoparticles (ZnO NPs) under conventional conditions, with heating (at 60 and 80°C and under reflux) compared with ultrasonic. The effect of solvent was investigated to reveal that the solvent system CH3CN/H2O was optimum to obtain 1-substituted 1H-tetrazole in high yield. In addition, the effect of irradiation power was studied, which showed that the yield of the reaction was improved at 200 W and the reaction time was shortened to be 30 min. Also, an improvement in the rate of the reaction and the yield of the products was observed when reactions were carried out under sonication conditions in the presence of ZnO NPs compared with conventional methods using various zinc salts as catalysts. The yields of tetrazole compounds 2a–i under sonication were determined (88–96percent). Furthermore, the investigated heterogeneous catalytic system was recycled and reused for five runs with significant production of tetrazole 2a as a model target compound in excellent yields at each reaction cycle. In general, the investigated synthetic strategy for the heterocyclization of α-amino acid ethyl ester derivatives to 1-substituted 1H-tetrazoles was in agreement with the green chemistry point of view.
Copper nanoparticles: A capable and versatile catalyst for the synthesis of diverse 1-phenyl-1H-tetrazoles from amino acids
Ariannezhad, Maryam,Habibi, Davood,Heydari, Somayyeh
, p. 170 - 179 (2019/01/15)
Cu nanoparticles were prepared in successive stages: preparation of the Fe3O4 magnetic nanoparticles (Fe3O4 MNPs), coating of the Fe3O4 MNPs with tetraethyl orthosilicate (Fe3Os
Synthesis of chiral α-(tetrazol-1-yl)-substituted carboxylic acids
Zarezin, Danil P.,Shmatova, Olga I.,Nenajdenko, Valentine G.
, p. 364 - 365 (2018/08/10)
Optically active α-(tetrazol-1-yl)-substituted carboxylic acid OBO-esters were synthesized from the corresponding a-isocyano OBO-esters and trimethylsilyl azide in up to 92% yield. Subsequent acidic hydrolysis proceeds without epimerization and makes it p
Synthesis of new 1-substituted-1h-1,2,3,4-tetrazoles from l-α-amino acids and their biological assays
Habibi, Davood,Rahmani, Payam,Ahmadi, Fatemeh,Bokharaei, Hanieh,Kaboudvand, Zahra
, p. 145 - 151 (2014/03/21)
A new series of 1-substituted 1H-1,2,3,4-tetrazoles was synthesized from the reaction of L-α-amino acids, triethylorthoformate and sodium azide in glacial acetic acid at 80 °C in good yields (55-80 %). Not only acetic acid is a good solvent but also an effective catalyst promoting the reaction compared with the Lewis acids/microwave, Lewis acids/ ultrasonic or Lewis acids/solvent-free conditions to give the corresponding 1H-1,2,3,4-tetrazoles. Also, the antimicrobial activity investigations (antibacterial activity against E. coli and antifungal activity against Candida albicans) showed that all the tetrazoles obtained were inactive except the one obtained from tryptophan. In addition, the obtained 1- substituted 1H-1,2,3,4-tetrazoles were resistant in different reducing and oxidizing conditions.
