31694-90-3Relevant academic research and scientific papers
Iron-promoted sulfur sequestration for the substituent-dependent regioselective synthesis of tetrazoles and guanidines
Pendem, Venkata Bhavanarushi,Tamminana, Ramana,Nannapaneni, Madhavi
, p. 499 - 509 (2021/04/09)
We have established a facile and versatile synthetic methodology for the construction of tetrazoles and guanidines in the presence of an eco-friendly, inexpensive, easily available iron reagent. Aromatic thioureas with electron-donating substituents produced their respective target products in quantitative yield. In contrast, when electron-withdrawing substituted aromatic thioureas were used, the expected products were obtained in reduced yield. However, the desired products were obtained in good yield at moderate temperature. In addition, mechanistic studies revealed that the synthetic route involved iron-based subsequent reactions of addition and removal of sulfur.
Selective Gold-Catalysed Synthesis of Cyanamides and 1-Substituted 1H-Tetrazol-5-Amines from Isocyanides
?koch, Karel,Císa?ová, Ivana,?těpni?ka, Petr
supporting information, p. 13788 - 13791 (2018/09/14)
The newly discovered gold-catalysed reaction of isocyanides with hydrazoic acid generated in situ from trimethylsilyl azide and methanol (or, alternatively, from NaN3/AcOH) produces either cyanamides or 1-substituted 1H-tetrazol-5-amines, depending on the amount of available HN3. The reaction proceeds selectively and in generally high yields of either product, thus providing a particularly convenient access to a wide range of substituted 1H-tetrazol-5-amines that are rather difficult to access otherwise.
Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles
Andrejevi?, Tina P.,Nikoli?, Andrea M.,Gli?i?, Biljana ?.,Wadepohl, Hubert,Vojnovic, Sandra,Zlatovi?, Mario,Petkovi?, Milo?,Nikodinovic-Runic, Jasmina,Opsenica, Igor M.,Djuran, Milo? I.
supporting information, p. 325 - 333 (2018/08/28)
Herein, we report the synthesis and structural characteristics of three tetrazole-containing compounds, 1-benzyl-1H-tetrazole (bntz), 1-benzyl-1H-tetrazol-5-amine (bntza) and 1-(4-methoxybenzyl)-1H-tetrazol-5-amine (mbntza) and the corresponding silver(I) complexes of the general formula [Ag(NO3-O)(L-N4)2]n, L = bntz (1), bntza (2) and mbntza (3). Silver(I) complexes 1–3 and 1-benzyl-1H-tetrazoles have been studied in detail by NMR, IR and UV–Vis spectroscopic methods and the structures of 1 and 2 have been determined by single-crystal X-ray diffraction analysis. The results of these analyses revealed a monodentate coordination of the ligands to Ag(I) ion via the N4 tetrazole nitrogen. The antimicrobial potential of silver(I) complexes 1–3 was evaluated against the broad panel of Gram-positive and Gram-negative bacteria and fungi, displaying their remarkable inhibiting activity with MIC (minimal inhibitory concentration) values in the range 2–8 and 0.16–1.25 μg/mL (3.8–16.3 and 0.31–2.15 μM), respectively. On the other hand, 1-benzyl-1H-tetrazoles used for the synthesis of the silver(I) complexes were not active against the investigated strains, suggesting that the activity of the complexes originates from the Ag(I) ion exclusively. Moreover, silver(I) complexes 1–3 have good therapeutic potential, which can be deduced from their moderate cytotoxicity on the human fibroblast cell line MRC5, with IC50 values falling in the range 30–60 μg/mL (57.7–103.4 μM).
Cobalt-promoted one-pot reaction of isothiocyanates toward the synthesis of aryl/alkylcyanamides and substituted tetrazoles
Seelam, Mohan,Kammela, Prasada Rao,Shaikh, Bajivali,Tamminana, Ramana,Bogiri, Sujatha
, p. 535 - 544 (2018/07/05)
[Figure not available: see fulltext.] The synthesis of cyanamides and tetrazoles from isothiocyanates through tandem reaction using cobalt catalyst has been demonstrated. In the case of tetrazole preparation, the reaction involved addition/desulfurization/nucleophilic addition/electrocyclization, whereas aromatic cyanamides were constructed from isothiocyanates through addition/desulfurization. Cheap cobalt sulfate was used for the synthesis of various cyanamides and tetrazoles. In addition, cobalt catalyst was found to be desulfurization reagent that has not been previously reported. The final products have been obtained from starting precursors in good to high yield.
1-Substituted 5-aminotetrazoles: Syntheses from CNN3 with primary amines
Joo, Young-Hyuk,Shreeve, Jean'ne M.
supporting information; experimental part, p. 4665 - 4667 (2009/05/13)
(Chemical Equation Presented) 1-Substituted 5-aminotetrazoles were prepared in situ by an excellent reaction of cyanogen azide and primary amines to generate an imidoyl azide as an intermediate in acetonitrile/water. After cyclization, the intermediate ga
One Dimensional Copper(II) Coordination Polymers: Crystal Engineering through Variable Types of Linkage [1]
Saalfrank, Rolf W.,Harbig, Roland,Struck, Oliver,Hampel, Frank,Peters, Eva Maria,Peters, Karl,Von Schnering, Hans Georg
, p. 125 - 134 (2007/10/03)
Reaction of a methanolic copper(II) acetate solution with tetrazolyl enol derivatives 2a or 2b leads to the formation of the corresponding 1D-coordination polymer 1∞[CuL2] 3a and pseudo 1D-coordination polymer [CuL2]2 3b, respectively. On the contrary, reaction of 2c with methanolic copper(II) acetate solution yields OH-bridged 1D-coordination polymer 1∞[CuL2(MeOH)2] 3c. Single-crystal X-ray diffraction of the supramolecular species 3 established unequivocally the structures of the stairlike coordination compounds. Reaction of a methanolic copper(II) acetate solution with amidotetrazole derivative 6 leads to the formation of the 1D-coordination polymer 1∞[CuL2] 7. The structure of 7 has been established by X-ray structure analysis.
