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Tandem transformations of 1,2,4-triazol-5-ylidenes into 5-amidino-1,2,4-triazoles

Authors: Korotkikh, Nikolai I.; Glinyanaya, Natalia V.; Cowley, Alan H.; Moore, Jennifer A.; Knishevitsky, Arthur V.; Pekhtereva, Tatyana M.; Shvaika, Oles P.;

Tandem transformations of 1,2,4-triazol-5-ylidenes into 5-amidino-1,2,4-triazoles

Abstract

The first tandem autotransformations of heteroaromatic carbenes have been found. These reactions involve cleavage of the 1-tert-butyl-3,4-diaryl-1,2,4-triazol-5-ylidenes 1a-d to form benzonitriles and the respective carbodiimides, followed by further reactions of the latter with carbenes 1a-d to afford the 3,4-diaryl-5-(1-tert-butyl-3-arylamidin-2-yl)-1,2,4-triazoles 5a-d. The X-ray structures of the carbene 1-tert-butyl-3-phenyl-4-n-bromophenyl-1,2,4-triazol-5- ylidene (1a) and the amidinotriazole 3-phenyl-4-p-bromophenyl-5-(1-tert-butyl-3-p- bromophenylamidin-2-yl)-1,2,4-triazole (5a) were determined. The reactions of 1a with the electrophiles diphenylcarbodiimide, acetonitrile, and diphenyldiazomethane are also described.

Country
United States
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Keywords

stable carbene, organic, Organic chemistry, tandem autotransformations, chemistry, 540, n-heterocyclic carbenes, carbenes, cleavage reactions, reactivity, azines, QD241-441, 1,3,4-triphenyl-4,5-dihydro-1h-1,2,4-triazol-5-ylidene, triazoles

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citations
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
12
Average
Average
Average
gold
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