- 1-Disulfo-[2,2-bipyridine]-1,1-diium chloride ionic liquid as an efficient catalyst for the green synthesis of 5-substituted 1H-tetrazoles
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A simple, green and efficient method has been developed for the synthesis of 5-substituted 1H-tetrazole derivatives through [2+3] cycloaddition reaction in good to excellent yields between various benzonitriles and sodium azide. For this purpose, 1-disulfo-[2,2-bipyridine]-1,1-diium chloride ([BiPy](HSO3)2Cl2) system as an ionic liquid catalyst have been extended for the construction of these valuable products. This procedure has significant advantages, including using ethylene glycol as a green solvent. The other advantages of this method are inexpensive and ease the preparation of the catalyst, mild reaction conditions, green reaction medium, easy workup, short reaction time, and simple experimental process.
- Aali, Elaheh,Gholizadeh, Mostafa,Noroozi-Shad, Nazanin
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- Construction of Bicyclic 1,2,3-Triazine N-Oxides from Aminocyanides
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Using a facile and cost-effective method, nine bicyclic 1,2,3-triazine 2-oxides were synthesized from o-aminocyanide substrates through an unusual nitration cyclization. The reaction mechanism was studied experimentally and theoretically. Moreover, nine 1
- Liu, Yuji,Qi, Xiujuan,Zhang, Wenquan,Yin, Ping,Cai, Ziwu,Zhang, Qinghua
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supporting information
p. 734 - 738
(2021/01/09)
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- Syntheses of 5-substituted 1H-tetrazoles catalyzed by reusable Cu(II)-NaY zeolite from nitriles
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Cu(II)-NaY heterogeneous catalyst is used for the synthesis of 5-substituted 1H-tetrazoles by [2+3]-cycloaddition of sodium azide and nitriles. The salient features of this process are low reaction times, mild reaction conditions and high yields. The catalyst is recovered and reused for several cycles with consistent activity.
- Sudhakar,Purna Chandra Rao,Prem Kumar,Suresh,Ravi
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p. 864 - 866
(2017/02/10)
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- Choline chloride–ZnCl2: Recyclable and efficient deep eutectic solvent for the [2+3] cycloaddition reaction of organic nitriles with sodium azide
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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
- Padvi, Swapnil A.,Dalal, Dipak S.
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supporting information
p. 779 - 787
(2017/04/06)
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- Method for preparing tetrazole compound
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The invention discloses a method for preparing a tetrazole compound. The tetrazole compound is synthesized/prepared from cyanobenzene or substituted cyanobenzene and sodium azide, which serve as raw materials, in a manner of taking dimethylformamide as a
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Paragraph 0033; 0034; 0047; 0048
(2017/08/28)
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- Activated Fuller's earth as an inexpensive, eco-friendly, efficient catalyst for the synthesis of 5-aryl 1-H-tetrazole via [3+2] cycloaddition of nitriles and sodium azide
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A simple and efficient method for the preparation of 5-aryl 1-H-tetrazoles was developed from various aryl nitriles and sodium azide (NaN3) via [3+2] cycloaddition reaction using activated Fuller's earth as an efficient heterogeneous catalyst.
- Rekunge, Deelip S.,Indalkar, Krishna S.,Chaturbhuj, Ganesh U.
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supporting information
p. 5815 - 5819
(2016/12/06)
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- Ni-S-methylisothiourea complexes supported on boehmite nanoparticles and their application in the synthesis of 5-substituted tetrazoles
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Boehmite nanoparticles are aluminum oxide hydroxide (γ-AlOOH) particles, which were prepared by a simple and inexpensive procedure and immobilized further with nickel-S-methylisothiourea complexes (Ni-SMTU@boehmite), and characterized by FT-IR spectroscopy, TGA, XRD, ICP-OES, EDS, SEM and TEM techniques. Finally, we investigated the catalytic activity of Ni-SMTU@boehmite as a new, heterogeneous, stable and highly reusable nanocatalyst for the synthesis of 5-substituted 1H-tetrazole derivatives in PEG-400 as a green solvent. This catalyst was recovered by simple filtration and reused several times without significant loss of its catalytic efficiency or nickel leaching. The heterogeneity of this catalyst has been studied using hot filtration and ICP-OES technique.
- Ghorbani-Choghamarani, Arash,Moradi, Parisa,Tahmasbi, Bahman
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p. 56638 - 56646
(2016/07/06)
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- Synthesis of 6-N-R-tetrazolo[1,5-c]quinazolin-5(6H)-ones and their anticancer activity
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Chemical compounds with tetrazole ring are very interesting systems that can be valuable in pharmaceutical and clinical applications, especially as anticancer agents. In this work, novel 6-N-R-tetrazolo[1,5-c]quinazolin-5(6H)-ones were synthesized. A large set of IR, LC-, EI-MS, 1H, 13C NMR and elemental analysis data were collected and evaluated for their structures and purity. Details of synthesis, namely the N-alkylation, are discussed, including reactions with secondary and tertiary amides. Four new synthesized compounds (2.7, 3.2, 5.2, 5.3) were tested in vitro for anticancer activity at 10 μM against 60 cell lines of nine different cancer types: leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers. Further synthesis of substances within the series of substituted tetrazolo[1,5-c]quinazoline systems will be attempted to develop improved compounds with better anticancer activity.
- Antypenko, Oleksii,Kovalenko, Sergiy,Rasulev, Bakhtiyor,Leszczynski, Jerzy
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p. 638 - 645
(2016/10/06)
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- Expeditious Synthesis of 2-Phenylquinazolin-4-amines via a Fe/Cu Relay-Catalyzed Domino Strategy
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A highly efficient Fe/Cu relay-catalyzed domino protocol has been developed for the synthesis of 2-phenylquinazolin-4-amines from commercially available ortho-halogenated benzonitriles, aldehydes, and sodium azide. This elegant domino process involved con
- Jia, Feng-Cheng,Zhou, Zhi-Wen,Xu, Cheng,Cai, Qun,Li, Deng-Kui,Wu, An-Xin
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supporting information
p. 4236 - 4239
(2015/09/15)
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- Synthesis of 5-substituted 1H-tetrazoles using a recyclable heterogeneous nanonickel ferrite catalyst
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An efficient method was developed for the [2 + 3] cycloaddition of sodium azide with nitriles to afford 5-substituted 1H-tetrazoles using nanonickel ferrite (NiFe2O4) as an effective heterogeneous catalyst in dimethylformamide. The main advantages of this method are high yields, simple methodology and easy work-up. The catalyst can be recovered and reused for several cycles with predictable activity.
- Abrishami, Fatemeh,Ebrahimikia, Maryam,Rafiee, Fatemeh
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p. 730 - 735
(2015/11/09)
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- Mesoporous AlPO4: A highly efficient heterogeneous catalyst for synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide via [3 + 2] cycloaddition
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The mesoporous AlPO4 with high surface area and fine mesoporous structure was prepared by a soft template method and showed excellent catalytic performance for synthesis of 5-substituted 1H-tetrazoles from various nitriles and sodium azide with
- Ai, Man,Lang, Leiming,Li, Baojun,Xu, Zheng
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supporting information; experimental part
p. 814 - 816
(2012/09/22)
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- Fe3O4/ZnS hollow nanospheres: A highly efficient magnetic heterogeneous catalyst for synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide
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An efficient route for the synthesis of 5-substituted 1H-tetrazole via [2+3] cycloaddition of nitriles and sodium azide is reported using Fe 3O4/ZnS hollow nanospheres as a magnetic separable heterogeneous catalyst. The catalyst is very efficient, affording excellent yields and can be reused for several circles. In addition, the Fe 3O4 inner shell exhibits magnetism, making the catalyst easily separated by a magnet. The catalyst can be easily separated by a magnet for further reuse. After reused for three times, the catalytic activity can maintain 90% of the initial value and exhibits good magnetism. Copyright
- Qi, Gang,Liu, Wei,Bei, Zhining
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scheme or table
p. 131 - 134
(2012/03/27)
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- Mesoporous ZnS nanospheres: A high activity heterogeneous catalyst for synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide
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Mesoporous ZnS nanospheres is a novel heterogeneous catalyst for synthesis of 5-substituted 1H-tetrazoles from various nitriles and sodium azide with excellent catalytic performance.
- Lang, Leiming,Li, Baojun,Liu, Wei,Jiang, Li,Xu, Zheng,Yin, Gui
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supporting information; experimental part
p. 448 - 450
(2010/05/01)
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- γ-Fe2O3: A magnetic separable catalyst for synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide
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An efficient route for the synthesis of 5-substituted 1H-tetrazole via [2+3] cycloaddition of nitriles and sodium azide is reported using γ-Fe2O3 nanoparticles as a magnetic separable catalyst. Under optimized conditions, the moderate to good yields (71-95%) can be obtained. The catalyst can be easily separated by a magnet and reused for several circles.
- Qi, Gang,Dai, Yong
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scheme or table
p. 1029 - 1032
(2011/10/08)
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- Substituted phenyl derivatives, their preparation and use
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A compound having the formula (I) or a pharmaceutically acceptable salt thereof where the variables are defined in the specification are useful in the treatment of sickle-cell anemia.
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- Novel synthesis of 5-substituted tetrazoles from nitriles
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A variety of 5-substituted tetrazoles were prepared through the respective reactions of sodium azide with corresponding nitriles in an aromatic solvent in the presence of an amine salt.
- Koguro, Kiyoto,Oga, Toshikazu,Mitsui, Sunao,Orita, Ryozo
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p. 910 - 914
(2007/10/03)
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- Process for preparation of 5- substituted tetrazoles
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The invention is directed to a process for preparing a 5-substituted tetrazole, the process comprising the step of reacting a nitrile with an inorganic azide salt in an aromatic hydrocarbon solvent in the presence of an amine salt. According to the invention, a 5-substituted tetrazole can be produced in a high yield with ease and safety using inexpensive raw materials while the reaction is easily controlled to inhibit a side reaction.
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- Process for the preparation of tetrazoles
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The present invention relates to a process for the preparation of 5-aryl tetrazoles of the formula: STR1 or a salt thereof comprising reacting an aryl nitrile with a trisubstituted silyl azide and a disubstituted tin oxide.
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