Rapid One-Pot, Four-Step Synthesis of Highly Fluorescent 1,3,4,5-Tetrasubstituted Pyrazoles

Willy, Benjamin; Müller, Thomas J. J.

doi:10.1021/ol2004947

Cited by 102 publications

(44 citation statements)

References 51 publications

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“…Further elaboration of the previously reported concept afforded the transformation of the in situ generated 4-halo pyrazole 29 in the presence of catalytic metal complexes in a Suzuki-coupling [123]. In the sense of an assisted tandem catalysis, the addition of catalytic amounts of triphenylphosphane to the reaction mixture for the retention of the correct oxidation state of the Pd source gave rise to the formation of 1,3,4,5-tetrasubstituted pyrazoles 30 in a four-step sequence comprising Sonogashira-coupling, addition-cyclocondensation, halogenation, and Suzuki-coupling in a one-pot fashion (Scheme 20, Table 10).…”

Section: Scheme 19 Four-component Synthesis Of 4-halo Pyrazoles 29mentioning

confidence: 98%

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Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles

Lessing

Müller

2015

Applied Sciences

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Sequentially Pd-catalyzed processes are excellent entries to heterocycle synthesis. The broad mechanistic variety combined with often very mild reaction conditions allow the concatenation of elementary organic and organometallic steps to novel sequences in the sense of one-pot domino and multicomponent reactions. Given the numerous opportunities of alkyne coordination and their Pd-mediated transformations, alkynylation and carbometallation play a key role, both for purely organometallic sequences as well as in those processes that are intercepted by cyclocondensation. Pd-catalyzed aminations also find more and more entry into novel heterocycle syntheses based upon this theme.

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Section: Scheme 19 Four-component Synthesis Of 4-halo Pyrazoles 29mentioning

confidence: 98%

“…As an example the combination with an electrophilic halogenation led to a one-pot four-component sequence of 4-halo pyrazoles 29 (Scheme 19) [123].…”

Section: Sequences Intercepted By Cyclizationsmentioning

confidence: 99%

Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles

Lessing

Müller

2015

Applied Sciences

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“…For example, five-membered heterocycles are present in more than hundred drugs available in the market and approximately thousands of heterocyclic derivatives are under clinical trials [37]. Apart from this, they have also been known for their catalytic [38,39], fluorescent [40][41][42], and dying properties [43,44].…”

Section: Five-membered Ring Compoundsmentioning

confidence: 99%

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

et al. 2015

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One-pot heterocyclic synthesis is an exciting research area as it can open routes for the development of otherwise complex transformations in organic synthesis. Heterocyclic compounds show wide spectrum of applications in medicinal chemistry, chemical biology, and materials science. These heterocycles can be generated very efficiently through highly economical and viable routes using one-pot synthesis. In particular, the metal-free one-pot synthetic protocols are highly fascinating due to several advantages for the industrial production of heterocyclic frameworks. This comprehensive review is devoted to the transition metal-free one-pot synthesis of nitrogen-containing heterocycles from the period 2010-2013.

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“…These highly convergent strategies paved the way to luminescent push–pull dienes 1 – 4 with conformationally flexible and fixed acceptor units (Fig. 1) [30–32], pyrazoles [33–34], benzodiazepines [35], furans and pyrroles [36–37] by consecutive multicomponent reactions and to highly emissive spirocycles [38–40] and pyranoindoles [41] via domino sequences. Interestingly, our versatile three-component enaminone synthesis [42–43] could be readily extended in a vinylogous fashion with enamines furnishing orange or deep red diene chromophores 2 and 3 that display aggregation induced emission [31].…”

Section: Introductionmentioning

confidence: 99%

One-pot three-component synthesis and photophysical characteristics of novel triene merocyanines

Muschelknautz¹,

Visse²,

Nordmann³

et al. 2014

Beilstein J. Org. Chem.

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SummaryNovel triene merocyanines, i.e. 1-styryleth-2-enylidene and 4-(1,3,3-trimethylindolin-2-ylidene)but-2-en-1-ylideneindolones are obtained in good to excellent yields in a consecutive three-component insertion Sonogashira coupling–addition sequence. The selectivity of either series is remarkable and has its origin in the stepwise character of the terminal addition step as shown by extensive computations on the DFT level. All merocyanines display intense absorption bands in solution and the film spectra indicate J-aggregation. While 1-styryleth-2-enylideneindolones show an intense deep red emission in films, 4-(1,3,3-trimethylindolin-2-ylidene)but-2-en-1-ylideneindolones are essentially nonemissive in films or in the solid state. TD-DFT computations rationalize the charge-transfer nature of the characteristic broad long-wavelength absorptions bands.

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Rapid One-Pot, Four-Step Synthesis of Highly Fluorescent 1,3,4,5-Tetrasubstituted Pyrazoles

Cited by 102 publications

References 51 publications

Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles

Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

One-pot three-component synthesis and photophysical characteristics of novel triene merocyanines

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