1965
DOI: 10.1002/cber.19650981228
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1.3‐Dipolare Cycloadditionen, XXIII. Einige Beobachtungen zur Addition organischer Azide an CC‐Dreifachbindungen

Abstract: Wenngleich elektronenarme Azide sich bevonugt an elektronenreiche Alkine anlagern, lassen sich aus Tosylazid mit Acetylendicarbonsilureester, Propiolsttureester, Phenylpropiolsiluter und Phenylacetylen die I-Tosyl-1.2.3-triazole erhalten. Phenylazid tritt mit Methyl-propiolat zu 88 % 1 -Phenyl-triazol-4carbonester und 12 % des isomeren 5-Carbonesters zusammen. 4-Nitro-phenylazid addiert sich rascher als 4-Methoxy-phenylazid an khoxy-acetylen zum 1 -Aryl-5-ilthoxy-triazol. Bern-in, das als gespanntes Cycloalkin… Show more

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Cited by 295 publications
(116 citation statements)
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“…Owing to their importance an impressive number of work has been published on the chemistry and synthesis of 1,2,3-triazoles [5][6][7][8][9][10][11][12][13][14][15][16] . However, literature inspection indicated lack of efficient synthetic approach to 2-substituted-1,2,3-triazoleamines [15] .…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Owing to their importance an impressive number of work has been published on the chemistry and synthesis of 1,2,3-triazoles [5][6][7][8][9][10][11][12][13][14][15][16] . However, literature inspection indicated lack of efficient synthetic approach to 2-substituted-1,2,3-triazoleamines [15] .…”
Section: Resultsmentioning
confidence: 99%
“…However at this stage it seemed quite probable that may be our cyclization product is that isoxazole and literature product is really the 1,2,3-triazole. This possibility seemed in fact however, least likely as 13 C NMR of cyclization product in DMF revealed carbonyl carbon at δ 185.99 ppm. Conclusive evidence for structure has been obtained via inspection of X-ray structure of compound 5g (C.f.…”
Section: Methodsmentioning
confidence: 99%
“…Thus, azides are readily reduced to amines, amides or carbamates, act as precursors for nitrenes and as radical traps, and undergo a variety of named reactions including 1,3-dipolar cycloadditions and rearrangement processes. [1] From a practical point of view, in addition to their widely recognized utility for the synthesis of 1,2,3-triazoles, [4] azides are convenient and atom-economic protecting groups for primary amines [5,6,7] and have found use as photoaffinity reagents for biomolecules [8] and as bioorthogonal chemical reporters in biological systems. [2,9] Although azides are most commonly prepared by nucleophilic substitution of an appropriate leaving group by the azide anion, this approach is sometimes compromised by competing elimination processes or by poor stereochemical control.…”
Section: Introductionmentioning
confidence: 99%
“…2 Nowadays, click chemistry 3 represents a pivotal tool in the discovery of new therapeutic compounds and in medicinal chemistry since allows molecular diversity in a direct, precise and selective manner. 4 In particular, the Huisgen 1,3-dipolar cycloaddition of azides and alkynes 5 has become a synthetic cornerstone since the paramount discovery by the groups of Meldal 6 and Sharpless 7 of its copper(I)-catalysed version (CuAAC). 8 This powerful methodology, which is considered the paradigm of a click reaction, gives a straight access into the 1,2,3-triazole moiety with high reliability and selectivity.…”
Section: Introductionmentioning
confidence: 99%