69746-30-1Relevant academic research and scientific papers
Practical synthesis of tetrazoles from amides and phosphorazidates in the presence of aromatic bases
Ishihara, Kotaro,Ishihara, Kazuki,Tanaka, Yota,Shioiri, Takayuki,Matsugi, Masato
supporting information, (2022/02/02)
Tetrazoles were effectively synthesized from amides using diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate in the presence of aromatic bases. Various amides underwent the proposed cycloaddition reaction to provide the corresponding tetrazoles. Studies on the racemization of chiral substrates were also performed. Overall, the proposed synthesis method enables the preparation of 1,5-disubstituted and 1-substituted tetrazoles, and 5-substituted 1H-tetrazoles without using toxic or explosive reagents.
An Expeditious Approach to Tetrazoles from Amides Utilizing Phosphorazidates
Ishihara, Kotaro,Shioiri, Takayuki,Matsugi, Masato
supporting information, p. 6244 - 6247 (2020/07/24)
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
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.
A Study of Annular Tautomerism, Interannular Conjugation, and Methylation Reactions of ortho-Substituted-5-aryltetrazoles using Carbon-13 and Hydrogen-1 N.M.R. Spectroscopy
Butler, Richard N.,Garvin, Victor C.
, p. 390 - 393 (2007/10/02)
In ortho-substituted-5-phenyltetrazoles, Ar-CN4H (Ar = 2'-MeC6H4, 2'-ClC6H4, or 2',6'-Cl2C6H3), the rings are twisted out of the planar configuration and interannular conjugation is inhibited.In each case the tetrazole 1-NH tautomer is strongly predominan
TETRAZOLES. VIII. KINETICS AND RATIO OF THE REACTION PRODUCTS IN THE ALKYLATION OF THE SALTS OF SUBSTITUTED 5-PHENYLTETRAZOLES BY DIMETHYL SULFATE IN ACETONITRILE
Ostrovskii, V. A.,Shirobokov, I. Yu.,Koldobskii, G. I.
, p. 131 - 135 (2007/10/02)
The kinetics and the ratio of the reaction products were investigated for the alkylation of potassium salts of a series of substituted 5-phenyltetrazoles by dimethyl sulfate in acetonitrile.It was shown that with the salt at a concentration of less than 10-3M the corresponding tetrazolate ion enters into reaction with dimethyl sulfate.Electron-withdrawing substituents in the benzene ring reduce the rate of the alkylation reaction and help to increase the proportion of the N2 isomer in the reaction products.The rate constants for the reaction of substituted 5-phenyltetrazoles with dimethyl sulfate and the ratios of the isomeric tetrazoles formed during alkylation correlate with the ? constants of the substituents.
