- An Expeditious Approach to Tetrazoles from Amides Utilizing Phosphorazidates
-
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
- Ishihara, Kotaro,Shioiri, Takayuki,Matsugi, Masato
-
supporting information
p. 6244 - 6247
(2020/07/24)
-
- Stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via a Beckmann rearrangement facilitated by diphenyl phosphorazidate
-
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.
- Ishihara, Kotaro,Shioiri, Takayuki,Matsugi, Masato
-
supporting information
p. 1295 - 1298
(2019/04/13)
-
- Gold-catalyzed synthesis of tetrazoles from alkynes by Ci£ C bond cleavage
-
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.
- Gaydou, Morgane,Echavarren, Antonio M.
-
supporting information
p. 13468 - 13471
(2014/01/06)
-
- The conversion of secondary amides to tetrazoles with trifluoromethanesulfonic anhydride and sodium azide
-
Due to the interest in tetrazoles as medicinal agents, a new, mild one-step method for the conversion of amides to tetrazoles employing triphenylphosphine, diethyl azodicarboxylate, and trimethylsilyl azide was recently introduced. An alternate and equally simple method employing trifluoromethanesulfonic anhydride and sodium azide was devised. This method was used to synthesize a series of 1,5-substituted tetrazoles from readily available secondary amides. A 1H-substituted tetrazole was also synthesized by this method from an amide substituted with a cyanoethyl protecting group.
- Thomas
-
p. 767 - 768
(2007/10/02)
-