- Synthesis of 5-Aryl and Vinyl Tetrazoles by the Palladium-Catalyzed Cross-Coupling Reaction
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A coupling reaction of 1-benzyl-5-bromotetrazole with various aryl and vinyl boronic acids via the Suzuki type reaction is found to be a general and efficient reaction for the synthesis of aryl and vinyl tetrazoles.
- Yi, Kyu Yang,Yoo, Sung-eun
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Read Online
- One-Pot Suzuki-Hydrogenolysis Protocol for the Modular Synthesis of 2,5-Diaryltetrazoles
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2,5-Diaryltetrazoles are a diverse range of compounds of considerable interest within the field of photochemistry as a valuable precursor of the nitrile imine 1,3-dipole. Current literature approaches toward this heterocycle remain unsuitable for the prac
- Bertrand, Sophie,Jamieson, Craig,Livingstone, Keith
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supporting information
p. 7413 - 7423
(2020/07/07)
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- An Expeditious Approach to Tetrazoles from Amides Utilizing Phosphorazidates
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A novel method was developed for the synthesis of tetrazoles from amides utilizing diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate as both the activator of amide-oxygen for elimination and azide source. Various amides were converted into th
- Ishihara, Kotaro,Shioiri, Takayuki,Matsugi, Masato
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supporting information
p. 6244 - 6247
(2020/07/24)
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- Iron (III)-porphyrin Complex FeTSPP as an efficient catalyst for synthesis of tetrazole derivatives via [2?+?3]cycloaddition reaction in aqueous medium
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The metal complex (5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin-iron (III) chloride (FeTSPP) was new employed in an environmentally benign protocol as an efficient catalyst for a “click” chemistry approach for the synthesis of tetrazole and guanindinyltetrazole derivatives via [2?+?3] cycloaddition reaction of nitriles and azide derivatives in aqueous medium. The synthesized compounds were obtained in excellent yield, short reaction times and a recoverable catalyst.
- El-Remaily, Mahmoud Abd El Aleem Ali Ali,Elhady
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- Indium-, Magnesium-, and Zinc-Mediated Debenzylation of Protected 1 H -Tetrazoles: A Comparative Study
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5-Substituted 1-benzyltetrazoles are easily debenzylated to give the corresponding deprotected tetrazoles using dissolved metals under protic conditions: Mg/MeOH, In/MeOH, or Zn/MeCO 2 H are the procedures of choice for this transformation.
- Behloul, Cherif,Benlahrech, Meriem,Foubelo, Francisco,Nájera, Carmen,Yus, Miguel
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supporting information
p. 3430 - 3435
(2018/07/02)
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- Convergent Three-Component Tetrazole Synthesis
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A microwave-accelerated, simple, and efficient method for the construction of the 1,5-tetrazole scaffold was developed. It comprises a multicomponent reaction of an amine, a carboxylic acid derivative, and an azide source. On the basis of the availability of the archetypical starting materials, this method provided very versatile synthetic access to 1,5-disubstituted tetrazoles. The usefulness of this method was demonstrated in the synthesis of biologically important fused tetrazole scaffolds and the marketed drug cilostazol.
- Chandgude, Ajay L.,D?mling, Alexander
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p. 2383 - 2387
(2016/06/01)
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- METHOD FOR PRODUCING BIARYL COMPOUND
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Provided is a novel production method capable of producing a biaryl compound, which is useful as an intermediate for angiotensin II receptor blockers, economically under conditions suitable for industrial production. A production method of a biaryl compound of the formula [3] or a salt thereof, including reacting a 2-phenylazole derivative of the formula [1] or a salt thereof, with a benzene derivative of the formula [2] or a salt thereof in the presence of a metal catalyst, a base, and one or more kinds of compounds selected from the group consisting of (a) a monocarboxylic acid metal salt, (b) a dicarboxylic acid metal salt, (c) a sulfonic acid metal salt, and (d) a phosphate or phosphoric amide metal salt represented by RAxP(O)(OM)y wherein each symbol is as defined in the DESCRIPTION.
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- PROCESS FOR PRODUCTION OF BIPHENYL DERIVATIVE
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The invention provides a production method of a biaryltetrazole derivative useful as an intermediate for an angiotensin II receptor antagonist. The method comprises reacting an aryltetrazole derivative with a benzene derivative, deprotecting or reducing the resulting compound, and halogenating the deprotected or reduced compound
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- O -iodoxybenzoic acid mediated oxidative desulfurization initiated domino reactions for synthesis of azoles
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A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.
- Chaudhari, Pramod S.,Pathare, Sagar P.,Akamanchi, Krishnacharaya G.
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experimental part
p. 3716 - 3723
(2012/06/16)
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- Highly efficient synthesis of 5-substituted 1H-tetrazoles catalyzed by Cu-Zn alloy nanopowder, conversion into 1,5- and 2,5-disubstituted tetrazoles, and synthesis and NMR studies of new tetrazolium ionic liquids
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A series of 5-substituted 1H-tetrazoles were synthesized through [3+2] cycloaddition reactions between nitriles RCN and NaN3 in the presence of Cu-Zn alloy nanopowder as catalyst. The 1,5-dibutyl, 1-butyl-5-hexyl, 2,5-dibutyl, and 2-butyl-5-hexyl derivatives were then used as building blocks to synthesize several novel tetrazolium ionic liquids (ILs) with EtSO 4-, OTf-, and NTf2- counterions. Whereas alkylation of the 2,5-dialkyltetrazoles selectively gave the N-4 alkylated onium salts, with the 1,5-dialkyl derivatives approximately 1:1 mixtures of two tetrazolium salts were formed by alkylation at N-3 and N-4. The triflate and ethyl sulfate salts are room-temperature ILs that are hydrophilic, whereas the NTf2 salts are low-melting ILs and are hydrophobic. The resulting tetrazolium-based ionic liquids were studied by various multinuclear and 2D NMR techniques including natural abundance 15N and 1H/15N correlations.
- Aridoss, Gopalakrishnan,Laali, Kenneth K.
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experimental part
p. 6343 - 6355
(2011/12/03)
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- Efficient synthesis of 1,5-disubstituted tetrazoles
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A general method for the synthesis of 1,5-disubstituted tetrazoles from imidoylbenzotriazoles that involves mild reaction conditions and short reaction times. Georg Thieme Verlag Stuttgart.
- Katritzky, Alan R.,Cai, Chunming,Meher, Nabin K.
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p. 1204 - 1208
(2008/02/02)
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- REMEDIES FOR STRESS DISEASES COMPRISING MITOCHONDRIAL BENZODIAZEPINE RECEPTOR ANTAGONISTS
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A pharmaceutical composition for the prophylaxis and/or treatment of diseases induced, exacerbated or reignited by stressors comprising the compound of formula (I) wherein all symbols have the same meanings as described in the specification, etc. as an active ingredient.
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- Oxidation potential as a measure of the reactivity of anionic nucleophiles. Behaviour of different classes of nucleophiles
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Anodic peak potentials for 42 anionic nucleophiles are reported along with the rate constants for the reactions of the anions with benzyl chloride.By comparing these rate constants with those of the reactions of outer-sphere electron-transfer reagents (radical anions), it has been demonstrated that the reactions of the anions with benzyl chloride are typical single-step SN2 reactions as opposed to a two-step process comprising dissociative single electron transfer (SET) to benzyl chloride followed by radical combination.The data suggest that very electron-rich nucleophilic anions with potentials of -1.5 to -2.2 V (and more negative) with respect to the ferrocenium/ferrocene couple might participate in a SET reaction.The 42 anions studied included representatives of four classes of nucleophiles, viz. sulfur-, carbon-, oxygen- and nitrogen-centred anions.The previously observed correlation of rate constants and anodic peak potential was again found for these anions with the most reactive species having the most negative peak potentials.Correlations by class indicate that the sensitivity of rate constants to changes in peak potential is greatest (and equivalent) for the sulfur-, carbon- and oxygen-anions and for representatives with the same peak potential, the rate constants by class follow the order sulfur > carbon > oxygen.The nitrogen nucleophiles show a significantly lower sensitivity of rate constant to changes in peak potential than do the other three classes.
- Niyazymbetov, Murat E.,Rongfeng, Zhou,Evans, Dennis H.
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p. 1957 - 1962
(2007/10/03)
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- SYNTHESIS OF 1,5-SUBSTITUTED TETRAZOLES FROM SECONDARY THIOAMIDES
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A new, rather simple method for the conversion of thiamides and similar structures into 1,5-substituted tetrazoles is described.The procedure employs TMS-N3 and mild Lewis acid, like SnCl4 in an inert solvent at room temperature and leads to high yields.Such compounds are of increasing interest for their pharmaceutical properties.
- Lehnhoff, Stefan,Ugi, Ivar
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p. 801 - 808
(2007/10/02)
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- Novel regioselective N-alkylations of 5-substituted-2H-tetrazoles
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Regioselective alkylation of 5-substituted-2H-tetrazoles 1 to 2-alkyl derivatives 3 was achieved via decarboxylative alkylation with alkyl cyanoformates. Lesser selectivity was observed with chloroformates.
- Prhavc,Kobe
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p. 1925 - 1928
(2007/10/02)
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- Regiospecific Coordination of Ambidentate Tetrazoles to Cobalt Oximes
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A series of complexes of the type (n-Bu3P)Co(DH)2(5R-tetrazolate) (DH is the monoanion of dimethylglyoxime; R = CF3, CH3, C6H5, C6H5CH2, (CH3)2N, 4-FC6H4, and 3-FC6H4) have been prepared and characterized by conductance studies, elemental analyses, and 1H, 13C, 31P, and 19F NMR spectroscopy.Quantum-mechanical calculations (MINDO/3) indicate that the N1 nitrogens of the aromatic tetrazolate anion are slightly more nucleophilic than the N2, yet in each complex the ambidentate tetrazolate anion is coordinated to cobalt via the N2 nitrogen, showing that regiospecific coordination is sterically induced.This is in marked contrast to tetrazole complexes of platinum and palladium wherein both N1 and N2 bound tetrazoles are found in approximately equal abundances.These cobalt complexes react with alkyl halides such as CH3I and C6H5CH2Br to produce exclusively 1,5-disubstituted tetrazoles.None of the isomeric 2,5-disubstituted tetrazole is detected in these reactions in marked contrast to the reactions of sodium tetrazolates or gold, palladium, or platinum tetrazolate complexes with alkyl halides which produce mixtures of the 1,5- and 2,5-disubstituted tetrazoles.The crystal structure of n-Bu3PCo(DH)2(5-CF3-tetrazolate) was determined using three-dimensional X-ray diffraction techniques.The molecule crystallizes in the orthorhombic space group Pbca in a unit cell of dimensions a = 12.040(2) Angstroem, b = 21.531(3) Angstroem, c = 23.536(4) Angstroem, ρcalcd = 1.368 g/cm3, ρobsd = 1.374 g/cm3.Refinement converged to 5.4percent with 2525 independent reflections.The tetrazolato ring is coordinated to cobalt via N2 and is planar.The Co-P bond (2.263 Angstroem) is one of the shortest observed in LCo(DH)2X structures.The acute dihedral angle between the planes of the two glyoximato groups (10.4 deg) is among the largest dihedral angles observed in structures of this type.Surprisingly, the tetrazolato ring does not lie in the fold of the two glyoximato rings but is nearly normal to it.Thus, the regiospecificity of the alkylations of the coordinated tetrazolate with alkyl halides is sterically promoted.
- Takach, Nicolas E.,Holt, Elizabeth M.,Alcock, Nathaniel W.,Henry, Ronald A.,Nelson, John H.
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p. 2968 - 2979
(2007/10/02)
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