Rearrangement of 5-Substituted 5-Aminopentadienals

Fischer, Fabian; Berger, Daniel; Neuenschwander, Markus

doi:10.1002/(sici)1521-3773(19980817)37:15<2138::aid-anie2138>3.0.co;2-5

Cited by 5 publications

(2 citation statements)

References 3 publications

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“…The researchers isolated vinyl-tosylates, analogous compounds to those synthesized by Iwasawa, in moderate yields. In 2011, as part of a study on an aza-Bergman rearrangement of 1,2-dialkynylimidazole Kerwin reported an addition of thiophenol to an N -alkynyl imidazole (Scheme 36, equation 3) [64]. Interestingly, in this example the sulfur nucleophile adds to the β-carbon of the alkyne to give 130 in a 43% yield.…”

Section: Reactions Of N-alkynyl Azolesmentioning

confidence: 99%

“…Using this scaffold, these workers developed a molecular probe that led to the discovery of a novel class of p-38α docking-recognition site inhibitors [138]. In future studies, Kerwin investigated the ability of dialkynylimidazoles to induce apoptosis in A549 cancer cells, and the researchers also investigated whether aza-Bergman rearrangement rates could be used to predict cytotoxicity [64]. Bhattacharjee has also investigated the cytotoxicity of N -alkynyl pyrazoles [56].…”

Section: Applications Of N-alkynyl Azolesmentioning

confidence: 99%

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Preparation and Utility of N-Alkynyl Azoles in Synthesis

Reinus

Kerwin

2019

Molecules

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Heteroatom-substituted alkynes have attracted a significant amount of interest in the synthetic community due to the polarized nature of these alkynes and their utility in a wide range of reactions. One specific class of heteroatom-substituted alkynes combines this utility with the presence of an azole moiety. These N-alkynyl azoles have been known for nearly 50 years, but recently there has been a tremendous increase in the number of reports detailing the synthesis and utility of this class of compound. While much of the chemistry of N-alkynyl azoles mirrors that of the more extensively studied N-alkynyl amides (ynamides), there are notable exceptions. In addition, as azoles are extremely common in natural products and pharmaceuticals, these N-alkynyl azoles have high potential for accessing biologically important compounds. In this review, the literature reports of N-alkynyl azole synthesis, reactions, and uses have been assembled. Collectively, these reports demonstrate the growth in this area and the promise of exploiting N-alkynyl azoles in synthesis.

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Section: Reactions Of N-alkynyl Azolesmentioning

confidence: 99%

Section: Applications Of N-alkynyl Azolesmentioning

confidence: 99%

Preparation and Utility of N-Alkynyl Azoles in Synthesis

Reinus

Kerwin

2019

Molecules

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The Aminopropenal‐ and Aminopentadienal Rearrangement

Neuenschwander

2015

Helvetica Chimica Acta

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Scope and mechanism of the aminopropenal rearrangement are reviewed: Various 3‐acyloxy‐3‐dialkylaminopropenals (2, formed by addition of acids to ‘push‐pull’‐acetylenes 1) rearranged quantitatively to give 3‐acyloxyacrylic amides (3, Schemes 1 and 22). Since these activated enol esters reacted very selectively with amino groups of polyfunctional amino acids, ‘push‐pull’‐acetylenes are versatile peptide reagents. Similarly, 5‐X‐5‐dialkylaminopentadienals (38, formed by addition of acids to ‘push‐pull’‐enynes 37) could be rearranged (aminopentadienal rearrangement). In this case, the rearrangement 38→40→42 (Schemes 16 and 22) normally stopped at the level of the quite stable 2‐dialkylamino‐pyrylium salts 40. Ring opening 40→42 of these intermediates was quite tricky, but could be realized in several cases.

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Formation and Reactivity of 5-Aminopenta-2,4-Dienals

Delpech¹

2014

Advances in Heterocyclic Chemistry

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Rearrangement of 5-Substituted 5-Aminopentadienals

Cited by 5 publications

References 3 publications

Preparation and Utility of N-Alkynyl Azoles in Synthesis

Preparation and Utility of N-Alkynyl Azoles in Synthesis

The Aminopropenal‐ and Aminopentadienal Rearrangement

Formation and Reactivity of 5-Aminopenta-2,4-Dienals

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