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Literature DB >> 27041776

Synthesis of 2-aryl-2H-tetrazoles via a regioselective [3+2] cycloaddition reaction.

Abstract

A regioselective cycloaddition reaction of arenediazonium salts with trimethylsilyldiazomethane is reported. A series of 2-aryltetrazoles were obtained in good to moderate yields with wide functional group compatibility. Furthermore, this cycloaddition reaction opens the way to build up the versatile intermediate 2-aryl-5-bromotetrazole.

Entities: CellLine Chemical Disease Species

Keywords: 2H-Tetrazole; Silver catalysis; Trimethylsilyldiazomethane; [3+2] Cycloaddition

Year: 2016 PMID： 27041776 PMCID： PMC4810784 DOI： 10.1016/j.tetlet.2016.02.102

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

13 in total

1. Efficient synthesis of 2,5-disubstituted tetrazoles via the Cu2O-catalyzed aerobic oxidative direct cross-coupling of N-H free tetrazoles with boronic acids.

Authors: Yu Li; Lian-Xun Gao; Fu-She Han
Journal: Chem Commun (Camb) Date: 2012-02-03 Impact factor: 6.222

2. Copper-Promoted Trifluoromethanesulfonylation and Trifluoromethylation of Arenediazonium Tetrafluoroborates with NaSO2CF3.

Authors: Ke Zhang; Xiu-Hua Xu; Feng-Ling Qing
Journal: J Org Chem Date: 2015-07-24 Impact factor: 4.354

3. The development of copper-catalyzed aerobic oxidative coupling of H-tetrazoles with boronic acids and an insight into the reaction mechanism.

Authors: Chao-You Liu; Yu Li; Jin-Ying Ding; De-Wen Dong; Fu-She Han
Journal: Chemistry Date: 2014-01-21 Impact factor: 5.236

4. HM30181 Derivatives as Novel Potent and Selective Inhibitors of the Breast Cancer Resistance Protein (BCRP/ABCG2).

Authors: Sebastian C Köhler; Michael Wiese
Journal: J Med Chem Date: 2015-04-24 Impact factor: 7.446

5. Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis.

Authors: M J Genin; D A Allwine; D J Anderson; M R Barbachyn; D E Emmert; S A Garmon; D R Graber; K C Grega; J B Hester; D K Hutchinson; J Morris; R J Reischer; C W Ford; G E Zurenko; J C Hamel; R D Schaadt; D Stapert; B H Yagi
Journal: J Med Chem Date: 2000-03-09 Impact factor: 7.446

6. Developing new chemical tools for DNA methyltransferase 1 (DNMT 1): a small-molecule activity-based probe and novel tetrazole-containing inhibitors.

Authors: Biwei Zhu; Jingyan Ge; Shao Q Yao
Journal: Bioorg Med Chem Date: 2015-03-10 Impact factor: 3.641

7. Synthesis and activity of substituted heteroaromatics as positive allosteric modulators for α4β2α5 nicotinic acetylcholine receptors.

Authors: Zhuang Jin; Pasha Khan; Youseung Shin; Jingyi Wang; Li Lin; Michael D Cameron; Jon M Lindstrom; Paul J Kenny; Theodore M Kamenecka
Journal: Bioorg Med Chem Lett Date: 2013-11-28 Impact factor: 2.823

8. Silver-catalyzed regioselective [3+2] cycloaddition of arene-diazonium salts with 2,2,2-trifluorodiazoethane (CF3CHN2): a facile access to 2-aryl-5-trifluoromethyltetrazoles.

Authors: Zhen Chen; Shuang-Qing Fan; Yan Zheng; Jun-An Ma
Journal: Chem Commun (Camb) Date: 2015-11-28 Impact factor: 6.222