57761-70-3Relevant academic research and scientific papers
Facile preparation of 5-alkyl-1-aryltetrazoles with arenes, acyl chlorides, hydroxylamine, and diphenylphosphoryl azide
Shibasaki, Kaho,Togo, Hideo
, p. 1816 - 1830 (2020/11/19)
Successive treatment of arenes with acyl chlorides and AlCl3, the addition of water and removal of solvent, the reaction with NH2OH?HCl and K2CO3, and the reaction with diphenylphosphoryl azide and DBU under warming conditions gave the corresponding 5-alkyl-1-aryltetrazoles efficiently in good to moderate yields. The present method is one-pot transformation of arenes into 5-alkyl-1-aryltetrazoles using the Friedel-Crafts acylation and the Beckmann rearrangement under transition-metal-free conditions.
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.
O -iodoxybenzoic acid mediated oxidative desulfurization initiated domino reactions for synthesis of azoles
Chaudhari, Pramod S.,Pathare, Sagar P.,Akamanchi, Krishnacharaya G.
experimental part, p. 3716 - 3723 (2012/06/16)
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.
An expeditious route toward pyrazine-containing nucleoside analogues
Modha, Sachin G.,Trivedi, Jalpa C.,Mehta, Vaibhav P.,Ermolat'ev, Denis S.,Van Der Eyckens, Erik V.
supporting information; experimental part, p. 846 - 856 (2011/04/17)
An improved and convenient methodology for the synthesis of asymmetrically substituted pyrazines starting from 3,5-dichloropyrazin-2(1H)-ones has been elaborated. Several nucleoside analogues have been synthesized containing the pyrazine core as the organic base coupled with the sugar via a triazole linkage. The beneficial effect of microwave irradiation throughout the sequence has been demonstrated.
Direct C-H arylation and alkenylation of 1-substituted tetrazoles: Phosphine as stabilizing factor
Spulak, Marcel,Lubojacky, Richard,Senel, Petr,Kunes, Jiri,Pour, Milan
experimental part, p. 241 - 244 (2010/04/06)
(Chemical Equation Presented) Direct arylation and alkenylation of 1-substituted tetrazoles was achieved via Pd catalysis in the presence of CuI and Cs2CO3. Unlike the related reactions of imidazoles and purines, phosphine ligand was
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.
