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Relevant academic research and scientific papers

Efficient synthesis of tetrazole hemiaminal silyl ethers via three-component hemiaminal silylation

An efficient route to construct 2,5-disubstituted tetrazole hemiaminal silyl ethers via one-pot three-component hemiaminal silylation of 5-substituted tetrazoles, aldehydes, and silyl triflates was developed. Diverse 2,5-disubstituted tetrazole hemiaminal silyl ethers were obtained with 37?:?63->99?:?1 regioisomeric ratios. The regioselectivities of this reaction were significantly affected by steric hindrance and the conjugation effects of substitutions on the 5-position of tetrazoles.

A Practical Synthesis of 5-Substituted 1 H -Tetrazoles from Aldoximes Employing the Azide Anion from Diphenyl Phosphorazidate

5-Substituted 1 H -tetrazoles were effectively synthesized from aldoximes and diphenyl phosphorazidate (DPPA) under reflux conditions in xylenes. Various aldoximes underwent the cycloaddition reaction to afford the corresponding 5-substituted 1 H -tetrazoles in short reaction times and in good yields. Chiral aldoximes derived from amino acids also gave aminotetrazoles with almost no racemization.

The microwave-assisted synthesis of 5-substituted 1: H -tetrazoles via [3+2] cycloaddition over a heterogeneous Cu-based catalyst: Application to the preparation of 13N-labelled tetrazoles

The [3+2] cycloaddition between various nitriles and sodium azide proceeds smoothly in the presence of a new CuII catalyst in N-methyl-2-pyrrolidone (NMP) to give the corresponding 5-substituted 1H-tetrazoles. The desired tetrazoles were obtain

Zn/MeOH-Mediated Practical and Easy Detritylation of Protected 1-Trityltetrazoles

A practical and low-cost method for the detritylation of 1-titryltetrazoles using zinc and methanol is described. This procedure is versatile and efficient in the deprotection of several protected tetrazoles bearing aliphatic, aromatic, and heteroaromatic substituents, as well as some functional groups, without decomposition of the tetrazole ring.

Indium-Mediated Cleavage of the Trityl Group from Protected 1 H -Tetrazoles

On treatment with indium metal in MeOH-THF, trityl groups undergo reductive removal from 1H-protected tetrazoles (including aliphatic, aromatic, and heteroaromatic substituents), affording the corresponding free tetrazoles in excellent yields, without any decomposition of the tetrazole ring or reduction of any other group.

Reductive removal of the pivaloyl protecting group from tetrazoles by a naphthalene-catalyzed lithiation process

The reaction of various 1-pivaloyl-1H-tetrazoles with excess lithium and a catalytic amount of naphthalene (20 mol%) led, after treatment with methanol, to the corresponding free tetrazoles through reductive C-N bond cleavage. This methodology represents a reasonable alternative to other nonreductive protocols.

Detritylation of protected tetrazoles by naphthalene-catalyzed lithiation

Treatment of N-tritylated tetrazoles bearing aliphatic, aromatic, or heteroaromatic substituents (including functionalized ones) with lithium powder and a catalytic amount of naphthalene led to reductive removal of the trityl group to give excellent yields of the corresponding free tetrazoles without decomposition of the tetrazole ring. The detritylation process was successfully extended to several tetrazoles that are components of sartans, an interesting class of drugs. The chemoselectivity between trityl-tetrazole and trityl-amine bond-cleavage reactions was also studied. This method represents an efficient technique for deprotection of tritylated tetrazoles under non-acidic conditions. Georg Thieme Verlag Stuttgart, New York.

Copper-catalyzed synthesis of 5-substituted 1H-tetrazoles via the [3+2] cycloaddition of nitriles and trimethylsilyl azide

The [3+2] cycloaddition between various nitriles and trimethylsilyl azide proceeds smoothly in the presence of a CuI catalyst in DMF/MeOH, to give the corresponding 5-substituted 1H-tetrazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper azide species, followed by a successive [3+2] cycloaddition with the nitriles.

TBAF-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles under Solventless Conditions

Tetrabutylammonium fluoride (TBAF) is an efficient catalyst in the [3 + 2] cycloaddition reaction of organic nitriles 1 with trimethylsilyl azide (TMSN3) in solventless conditions. The corresponding 5-substituted 1H-tetrazoles 2 were obtained under mild conditions and in 80-97% yields.

tris(2-Perfluorohexylethyl)tin azide: A new reagent for preparation of 5-substituted tetrazoles from nitriles with purification by fluorous/organic liquid-liquid extraction

Summary: The synthesis of a new fluorous tin azide, (C6F13CH2CH2)3SnN3, is reported and this reagent is used to make tetrazoles in both traditional and phase-switching modes. In the traditional mode, the tin azide is reacted with nitriles followed by HCl cleavage to provide the tetrazoles and the fluorous tin chloride (which can be reconverted into the tin azide). In the switching mode, the initial tin tetrazole is purified by fluorous/organic liquid-liquid extraction prior to destannylation. This provides pure products even in incomplete reactions or with impure starting materials, but it only works for smaller nitriles.