132372-75-9Relevant articles and documents
OSU-6: A highly efficient, metal-free, heterogeneous catalyst for the click synthesis of 5-benzyl and 5-aryl-1H-tetrazoles
Nammalwar, Baskar,Muddala, Nagendra Prasad,Pitchimani, Rajasekar,Bunce, Richard A.
, p. 22757 - 22766 (2015)
OSU-6, an MCM-41 type hexagonal mesoporous silica with mild Br?nsted acid properties, has been used as an efficient, metal-free, heterogeneous catalyst for the click synthesis of 5-benzyl and 5-aryl-1H-tetrazoles from nitriles in DMF at 90 °C. This catalyst offers advantages including ease of operation, milder conditions, high yields, and reusability. Studies are presented that demonstrate the robust nature of the catalyst under the optimized reaction conditions. OSU-6 promotes the 1,3-dipolar addition of azides to nitriles without significant degradation or clogging of the nanoporous structure. The catalyst can be reused up to five times without a significant reduction in yield, and it does not require treatment with acid between reactions.
Choline chloride–ZnCl2: Recyclable and efficient deep eutectic solvent for the [2+3] cycloaddition reaction of organic nitriles with sodium azide
Padvi, Swapnil A.,Dalal, Dipak S.
, p. 779 - 787 (2017)
Herein we report first time choline chloride–zinc chloride based deep eutectic solvent is a green and efficient reaction medium for the [2+3] cycloaddition reaction of organic nitriles with sodium azide to afford the corresponding 5-substituted 1H-tetrazo
Glycerol mediated synthesis of 5-substituted 1H-tetrazole under catalyst free conditions
Nandre, Kamalakar P.,Salunke, Jagdish K.,Nandre, Jitendra P.,Patil, Vijay S.,Borse, Amul U.,Bhosale, Sidhanath V.
, p. 161 - 164 (2012)
We have developed simple, cost effective and environmentally benign protocol for the synthesis of 5-substituted 1H-tetrazoles via [2,3] cycloaddition reaction from organic nitriles and sodium azide in glycerol under catalyst free condition. The corresponding 5-substituted 1H-tetrazoles were obtained with good to excellent yields (68-95%).
β-Cyclodextrin-mediated highly efficient [2+3] cycloaddition reactions for the synthesis of 5-substituted 1H-tetrazoles
Patil, Dipak R.,Wagh, Yogesh B.,Ingole, Pravin G.,Singh, Kripal,Dalal, Dipak S.
, p. 3261 - 3266 (2013)
A β-cyclodextrin-promoted [2+3] cycloaddition reaction between nitriles and sodium azide in the presence of ammonium chloride in DMF at 120 °C is reported, affording various 5-substituted 1H-tetrazoles in good to excellent yields in short reaction times. The presence of β-CD renders the formation of a precipitate-like gel in the reaction media when heated. No precipitation occurs in the absence of NaN3 and NH4Cl. The precipitation responses with other salts such as LiCl and NiCl2 were weaker than with NH4Cl. In the present paper the application of supramolecular aggregates is reported for the [2+3] cycloaddition reaction. β-Cyclodextrin can be recovered and reused without any significant loss of activity.
Fe3O4@L-lysine-Pd(0) organic–inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles
Ashraf, Muhammad Aqeel,Liu, Zhenling,Li, Cheng,Zhang, Dangquan
, (2021)
An efficient and sustainable synthetic protocol has been presented to synthesis and 5-substituted 1H-tetrazole privileged heterocyclic substructures. The synthetic protocol involves two-component reaction between aryl nitriles and NaN3 in water using complex of L-lysine-palladium nanoparticles (NPs) modified Fe3O4 nanoparticles as magnetically separable, recyclable, and reusable heterogeneous catalyst. Magnetically retrievable L-lysine-Pd(0) modified Fe3O4 nanoparticles were applied in [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles. The advantages of this strategy include easy recovery and efficient reusability of the expensive Pd NPs, obtaining high yields of [2 + 3] cycloaddition, short reaction times, and all of the reported synthetic strategies are being performed in water as green solvent for a wide range of substrates.
Ammonium acetate mediated synthesis of 5-substituted 1H-tetrazoles
Patil, Dipak R.,Deshmukh, Mukesh B.,Dalal, Dipak S.
, p. 799 - 803 (2012)
Synthesis of 5-substituted 1H-tetrazoles was achieved by [3+2] cycloaddition of nitriles and sodium azide in the presence of ammonium acetate. The reaction proceeds in situ formation of ammonium azide. Present protocol has advantage of good to excellent yields, short reaction times and simple isolation of products than reported methods. Iranian Chemical Society 2012.
Design, synthesis and evaluation of 5-substituted 1-H-tetrazoles as potent anticonvulsant agents
Liao, Ai-Mei,Wang, Tiantian,Cai, Bangrong,Jin, Yi,Cheon, Seunghoon,Chun, Chang Ju,Wang, Zengtao
, p. 435 - 443 (2017)
Abstract: A series of 5-substituted 1-H-tetrazoles were designed and synthesized as potent anticonvulsant agents. Their preliminary anticonvulsant activities were evaluated using maximal electroshock and subcutaneous pentylenetetrazole (scPTZ) seizure tests. Neurotoxicity was determined using rotarod test. The results indicated that the compound 2j in scPTZ model exhibited the ED50 values of 83.3?mg/kg, superior to the standard drug ethosuximide with the maximum activity. In addition, compound 2k showed the most potent activity in MES model with ED50 value of 9.6?mg/kg and TD50 value of 189.5?mg/kg after intraperitoneal injection in mice, and displayed a high protective index (TD50/ED50) of 19.7 compared to reference antiepileptic drugs. Graphical Abstract: [Figure not available: see fulltext.]
Lithiation Substitution of Unprotected Benzyltetrazoles
Wong, Jeff Y. F.,Lewandowska, Agnieszka,Trowse, Benjamin R.,Barker, Graeme
, p. 7069 - 7072 (2019/09/30)
1H-Tetrazoles occupy an important role in modern medicinal chemistry, but few methods for their modification exist. Many extant protocols require the use of a difficult to remove N-alkyl-protecting group, precluding the products from use as carboxylate bioisosteres, the major role of tetrazoles in pharmaceuticals. We herein report a convenient, protecting-group-free lithiation-substitution protocol for benzylic tetrazoles. Metalation with n-BuLi at 0 °C followed by electrophilic trapping gave a range of α-functionalized benzyltetrazoles in up to 91% yield.
Urea mediated 5-substituted-1H-tetrazole via [3?+?2] cycloaddition of nitriles and sodium azide
Yakambram,Jaya Shree,Srinivasula Reddy,Satyanarayana,Naveen,Bandichhor, Rakeshwar
supporting information, p. 445 - 449 (2018/01/03)
A simple, new and convenient metal free procedure for the synthesis of 5-substituted 1H-tetrazoles using various nitriles and sodium azide in the presence of urea and acetic acid with good to high yields is developed. The reaction plausibly proceeds through in situ formation of urea azide active complex without toxic and/or expensive metal catalysts.
Green synthesis of 5-substituted-1H-1,2,3,4-tetrazoles and 1-sustituted-1H-1,2,3,4-tetrazoles via [3+2] cycloaddition by reusable immobilized AlCl3on -Al2O3
Nanjundaswamy, Hemmaragala Marishetty,Abrahamse, Heidi
, p. 2137 - 2150 (2015/01/09)
We report the effectiveness of the surface modified γ-Al2O3which is reusable, efficient, catalytic, safe and environmentally acceptable procedure for the conversion of both alkyl and aryl nitriles into the corresponding 5-substituted-1H-1,2,3,4-tetrazoles via [3+2] cycloaddition with sodium azide in excellent yields at mild reaction conditions (50 ° C). The catalyst also afforded 1-substituted-1H-1,2,3,4-tetrazoles by the reaction of amines, sodium azide and triethyl orthoformate. The catalyst could be recycled and was reused eleven runs without losing its activity.
