1992
DOI: 10.1055/s-1992-26206
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1,2,4-Triazolium Salts from the Reaction of 1-Aza-2-azoniaallene Salts with Nitriles

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Cited by 67 publications
(52 citation statements)
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“…Analogously, the heteroallene 7 carrying a tert-butyl group were used to synthesize neutral 2-substituted 1,2,4-triazoles [30,31]. Compounds 7, which formed at low temperature from 6 [15,18] and SbCl 5 , reacted with the isothiocyanate 9 via C S cycloaddition to give the nitrilium ion 13a as an intermediate.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Analogously, the heteroallene 7 carrying a tert-butyl group were used to synthesize neutral 2-substituted 1,2,4-triazoles [30,31]. Compounds 7, which formed at low temperature from 6 [15,18] and SbCl 5 , reacted with the isothiocyanate 9 via C S cycloaddition to give the nitrilium ion 13a as an intermediate.…”
Section: Resultsmentioning
confidence: 99%
“…• C, 20a-c rearranged spontaneously by migration of the alkyl group at C-3 , via [1,2-shift] [30,34] to N-2 accompanied by the elimination of the CClR 1 R 2 group at N-1 , leading to the protonated 1,2,4-triazolium salts 21a-c. In situ deprotonation with aqueous NaHCO 3 [30,31] 33 were attributed to the methyl groups at C-5 of the triazole ring.…”
Section: Resultsmentioning
confidence: 99%
“…In our recent work, these cations have been utilized in the synthesis of new types of 1,2,4-triazoles such as C-nucleosides [14,15], acyclic C-nucleosides [16], pyrimidines [17], N-alkylphthalimides [18], D-mannopentitol-1-yl-1,2,4-triazoles [19], 1H-indoles [20], quinolones [20], benzotriazoles [21], 3 -triazolo-thymidines [22], acetic acid alkylidene hydrazides [23], and 1,4-disubstituted piperazines [24,25]. The reactive intermediates (4) were obtained from the α,α -dichloroazo compounds 3 [13] by treatment with SbCl 5 at −60…”
Section: Resultsmentioning
confidence: 99%
“…• C, 4 rearranged to protonated triazole 5 by [1,2] migration [39,40] Next, condensation of 6a-d with piperazine in the ratio of (2:1) in the presence of NaH or K 2 CO 3 and DMF at 25…”
Section: Resultsmentioning
confidence: 99%