14213-16-2Relevant articles and documents
5-Benzyl-1H-tetrazols from the reaction of 1-aryl-5-methyl-1H-tetrazoles with 1,2-dehydrobenzene
Aly, Ashraf A.,Shaker, Raafat M.
, p. 2679 - 2682 (2005)
A series of 1-aryl-5-benzyl-1H-tetrazoles has been obtained during the reaction of 1-aryl-5-methyl-1H-tetrazoles with 1,2-dehydrobenzene. The mechanism of product formation was investigated.
Reductive Fragmentation of Tetrazoles: Mechanistic Insights and Applications toward the Stereocontrolled Synthesis of 2,6-Polysubstituted Morpholines
Duchamp, Edouard,Simard, Benoit Deschênes,Hanessian, Stephen
supporting information, p. 6593 - 6596 (2019/09/30)
A new methodology to synthesize 2,6-di-, and 2,2′,6-trisubstituted morpholines via the reduction of oxabicyclic tetrazoles under mild conditions is described. The reaction proved successful for a wide range of tetrazoles, including sterically encumbered ones harboring gem-substituents on tertiary carbon centers. The mechanism for the decades-old reduction of tetrazoles to secondary amines is elucidated.
Stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via a Beckmann rearrangement facilitated by diphenyl phosphorazidate
Ishihara, Kotaro,Shioiri, Takayuki,Matsugi, Masato
supporting information, p. 1295 - 1298 (2019/04/13)
A novel method for the stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via the Beckmann rearrangement was developed using diphenyl phosphorazidate (DPPA) as both the oxime activator and azide source. Various ketoximes were transformed into the corresponding 1,5-disubstituted tetrazoles with exclusive trans-group migration and no E-Z isomerization of the ketoxime. This method enables the preparation of 1,5-disubstituted tetrazoles without using toxic or explosive azidation reagents.
An efficient synthesis of nitrile, tetrazole and urea from carbonyl compounds
Sribalan, Rajendran,Sangili, Arumugam,Banuppriya, Govindharasu,Padmini, Vediappen
, p. 3414 - 3421 (2017/07/13)
An efficient conversion of carbonyl compounds (aldehydes and ketones) to nitrile, tetrazole, and urea was developed with the use of a POCl3 and sodium azide mixture using a convergent and microwave method. This is the first report on the direct conversion of ketone to urea. The synthesized compounds were characterized by 1H NMR, 13C NMR, mass and IR spectroscopies and were found to be in agreement with reported compounds.
Gold-catalyzed synthesis of tetrazoles from alkynes by Ci￡ C bond cleavage
Gaydou, Morgane,Echavarren, Antonio M.
supporting information, p. 13468 - 13471 (2014/01/06)
Golden duality: Tetrazoles are formed by the reaction of alkynes with TMSN3 (TMS=trimethylsilyl) in the presence of iPrOH and the gold(I) catalyst [JohnPhosAu(MeCN)]SbF6. In this transformation gold plays a dual role, first activating the alkyne and then generating a Bronsted acid in situ.
Efficient synthesis of 1,5-disubstituted tetrazoles
Katritzky, Alan R.,Cai, Chunming,Meher, Nabin K.
, p. 1204 - 1208 (2008/02/02)
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.
α-ferrocenylalkylation of 1,5-disubstituted tetrazoles and certain transformations of reaction products
Krasnikova,Moskalenko,Kopaeva,Boev
, p. 1468 - 1475 (2007/10/03)
The reaction of α-hydroxyferrocenylalkyl derivatives and vinylferrocene with 1,5-disubstituted tetrazoles in methylene chloride-aqueous acid HX (X = BF4, ClO4) two-phase systems gives a mixture of 1,3,5- and 1,4,5-trisubstituted tetrazolium salts, the fraction of the 1,3,5-isomers prevailing. The synthesized salts are readily dealkylated under the action of bases to give the above starting compounds. Heating of 3(4)-(ferrocenylmethylene)-1,5-pentamethylenetetrazolium and 3(4)-(ferrocenylmethylene)-2-methyl-1-phenyltetrazolium tetrafluoroborates in anhydrous methanol or ethanol in the presence of catalytic amounts of alkali gives rise to ferrocenylcarbinol ethers. Other nuclephiles (pyridine, triphenylphosphine, sodium thiocyanate, sodium p-toluenesulfinate, dibenzoylmethane) also react with the above tetrazolium salts, forming ferrocenylmethylation products. Heating of equimolar amounts of 3(4)-(ferrocenylmethylene)-1,5-pentamethylenetetrazolium or 3(4)- (ferrocenylmethylene)-2-methyl-1-phenyltetrazolium perchlorates with mercury(II) perchlorates in anhydrous ethanol results in mercuration of the starting tetrazolium salts, involving hydrogen substitution in the methylene or methyl groups bound to tetrazolium carbon atoms. The condensation of the same salts with p-N,N-(dimethylamino)nitrosobenzene, leading to azomethine formation, occurs under similar conditions.
A facile and convenient synthesis of substituted tetrazole derivatives from ketones or α,β-unsaturated ketones.
El-Ahl, Abdel-Aziz S.,Elmorsy, Saad S.,Soliman, Hanan,Amer, Fathy A.
, p. 7337 - 7340 (2007/10/02)
Triazidochlorosilane (SiCl4-NaN3 in situ) is a new and efficient reagent for the direct conversion of ketones or α,β-unsaturated ketones to the corresponding tetrazole derivatives in nearly quantitative yield.
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.
5-(Diazomethyl)tetrazoles Substituted in Position 1 or 2 - A Comparative Study
Moderhack, Dietrich,Goos, Karl-Heinz
, p. 921 - 930 (2007/10/02)
The hitherto unknown title compounds 1 and 2 - readily obtained by amine diazotation (1) and Bamford-Stevens reaction (1, 2), respectively - show expected differences in both spectroscopic (UV/VIS,IR) and reactive behaviour towards (a) acids and electroph
