A Facile Synthesis of 2,5-Disubstituted Tetrazoles by the Reaction of Phenylsulfonylhydrazones with Arenediazonium Salts

Ito, Suketaka; Tanaka, Yasuhito; Kakehi, Akikazu; Kondo, Kenichi

doi:10.1246/bcsj.49.1920

Cited by 91 publications

(74 citation statements)

References 19 publications

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“…Compound 2, [9] N-Bocg-tosyl-homoserine-tert-butylester, [10] and all tetrazole compounds [18] were synthesized as previously described in literature. The silica gel used for flash column chromatography was received from Yantai Yuanbo Silica Gel Co.,C hina.…”

Section: Methodsmentioning

confidence: 99%

Protein Arginine Allylation and Subsequent Fluorophore Targeting

et al. 2013

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The inside cover picture shows protein methyltransferase-mediated alkylation in the presence of S-adenosyl-l-methionine (SAM) and its allylated analogue. On p. 1438 ff., Z. K. Zhang et al. relate how they discovered that allyl-SAM acts as an excellent SAM surrogate leading to protein allylation, and that the allyl group enables subsequent fluorophore targeting upon reaction with tetrazole compounds.

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Section: Methodsmentioning

confidence: 99%

Protein Arginine Allylation and Subsequent Fluorophore Targeting

et al. 2013

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“…First, the phenyl sulfonylhydrazones ( 23 ) react with the freshly prepared diazonium salts ( 24 ) in pyridine under cooled conditions to produce the desired tetrazole products ( 25 ) with moderate to good yields [25]. The hydrazones ( 23 ) can be synthesized easily from the aliphatic or aromatic aldehydes ( 21 ) and the diazonium salts from the corresponding amines with NaNO 2 under acidic conditions.…”

Section: Photoinduced 13-dipolar Cycloaddition Reaction Between Tementioning

confidence: 99%

Photo-Triggered Click Chemistry for Biological Applications

2015

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In the last decade and a half, numerous bioorthogonal reactions have been developed with a goal to study biological processes in their native environment, i.e., in living cells and animals. Among them, the photo-triggered reactions offer several unique advantages including operational simplicity with the use of light rather than toxic metal catalysts and ligands, and exceptional spatiotemporal control through the application of an appropriate light source with pre-selected wavelength, light intensity and exposure time. While the photoinduced reactions have been studied extensively in materials research, e.g., on macromolecular surface, the adaptation of these reactions for chemical biology applications is still in its infancy. In this chapter, we review the recent efforts in the discovery and optimization the photo-triggered bioorthogonal reactions, with a focus on those that have shown broad utility in biological systems. We discuss in each cases the chemical and mechanistic background, the kinetics of the reactions and the biological applicability together with the limiting factors.

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“…The title compound was synthesized using procedures adopted from multiple literature reports (Song et al, 2008;Ito et al, 1976). To a solution of 4-formylbenzoic acid (0.75 g, 5.0 mmol) in ethanol (50 ml) was added benzenesulfonohydrazide (0.86 g, 25 mmol) and the solution was stirred for 35 min.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Ammonium hydrogen bis[4-(2-phenyl-2H-tetrazol-5-yl)benzoate]

Janzen¹,

Lange²,

Wollack³

2016

IUCr Data

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The title salt, NH4 +·H+·2C14H9N4O2 −, is composed of an ammonium cation with a strong intermolecular negatively charge-assisted hydrogen-bonded acid/conjugate base-pair monoanion. The carboxylic acid H atom is located on an inversion center, while the N atom of the ammonium cation is located on a twofold rotation axis. In the crystal, the N—H bonds of each ammonium cation act as donors with carboxylate O-atom acceptors to form chains along the a-axis direction. The chains are linked by offset π–π interactions [intercentroid distances = 3.588 (2) and 3.686 (2) Å], forming layers parallel to the ab plane.

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A Facile Synthesis of 2,5-Disubstituted Tetrazoles by the Reaction of Phenylsulfonylhydrazones with Arenediazonium Salts

Cited by 91 publications

References 19 publications

Protein Arginine Allylation and Subsequent Fluorophore Targeting

Protein Arginine Allylation and Subsequent Fluorophore Targeting

Photo-Triggered Click Chemistry for Biological Applications

Ammonium hydrogen bis[4-(2-phenyl-2H-tetrazol-5-yl)benzoate]

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