28386-91-6Relevant articles and documents
Facile synthesis of 1,5-disubstituted tetrazoles by reacting a ruthenium acetylide complex with trimethylsilyl azide
Chang, Chao-Wan,Cheng, Ming-Chuan,Lee, Gene-Hsiang,Peng, Shie-Ming
, p. 11732 - 11742 (2019/08/13)
Treatment of [Ru]-CCPh (1, [Ru] = (η5-C5H5)(dppe)Ru, dppe = Ph2PCH2CH2PPh2) with trimethylsilyl azide afforded the cationic nitrile complex {[Ru]NCCH2Ph}[N3
Indium-, Magnesium-, and Zinc-Mediated Debenzylation of Protected 1 H -Tetrazoles: A Comparative Study
Behloul, Cherif,Benlahrech, Meriem,Foubelo, Francisco,Nájera, Carmen,Yus, Miguel
supporting information, p. 3430 - 3435 (2018/07/02)
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.
Efficient uncatalyzed conversion of primary and secondary thioamides into 1-substituted, 5-substituted, 1, 5-disubstituted and annulated tetrazoles
El-Ahl, Abdel-Aziz S.,Amer, Fatty A.,Elbeheery, Akram H.
experimental part, p. 2226 - 2235 (2012/03/26)
Unprecedented high-yield simple and mild conversion of primary aliphatic and aromatic thioamides into 5-substituted tetrazoles on treatment with a combination of tetrachlorosilane and sodium azide in refluxing acetonitrile has been achieved. Secondary acyclic, cyclic, and heterocyclic thioamides could also be transformed in high yields into 1-substituted, 1,5-disubstituted, or annulated tetrazoles under the same reaction condition. Copyright Taylor & Francis Group, LLC.
SYNTHESIS OF 1,5-SUBSTITUTED TETRAZOLES FROM SECONDARY THIOAMIDES
Lehnhoff, Stefan,Ugi, Ivar
, p. 801 - 808 (2007/10/02)
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.
Improved Schmidt synthesis of 1,5-disubstituted 1H-tetrazoles from ketones
Suzuki,Hwang,Nakaya,Matano
, p. 1218 - 1220 (2007/10/02)
On treatment with an excess of sodium azide in the presence of titanium(IV) chloride in boiling acetonitrile, both aliphatic and aromatic ketones are smoothly converted to 1,5-disubstituted 1H-tetrazoles in high yields.
Regiospecific Coordination of Ambidentate Tetrazoles to Cobalt Oximes
Takach, Nicolas E.,Holt, Elizabeth M.,Alcock, Nathaniel W.,Henry, Ronald A.,Nelson, John H.
, p. 2968 - 2979 (2007/10/02)
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.
