Pyrroles and N-Vinylpyrroles from Ketones and Acetylenes

Трофимов, Б. А.; Михалева, А. И.; Schmidt, Elena Yu.; Собенина, Л. Н.

doi:10.1016/s0065-2725(10)09907-1

Cited by 54 publications

(17 citation statements)

References 134 publications

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“…3‐Arylated (compounds 84 ) and 3,5‐diarylated (compounds 85 ) BODIPY dyes can be synthesized by one‐step, palladium‐catalyzed C–H arylation of 3,5‐unsubstituted boron dipyrrins 78 with aryl bromides (Scheme ) 44. This direct, transition‐metal‐catalyzed C–H functionalization is a much shorter synthetic protocol and a valuable alternative to the use of halogenated BODIPYs in traditional Suzuki and Stille cross‐coupling reactions28 or arylated pyrrole building blocks85–87 for constructing such BODIPY derivatives. Pd(OAc) 2 and tricyclohexylphosphine are the superior catalyst/ligand combination.…”

Section: Functionalization At the 3‐ And 35‐positionsmentioning

confidence: 99%

Postfunctionalization of the BODIPY Core: Synthesis and Spectroscopy

2015

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In this review we describe the various new methodologies for synthetic postmodification of the BODIPY core designed and developed by our research groups, as well as their electronic spectroscopic properties. We discuss the different strategies created for functionalization of the BODIPY framework at the pyrrole C‐ring positions and the meso‐position. Halogenated boron dipyrrins are substrates for nucleophilic substitution or Pd‐catalyzed cross‐coupling reactions. α‐Unsubstituted BODIPYs can be functionalized with N and C nucleophiles through oxidative or vicarious nucleophilic substitution (VNS) of the α‐hydrogen atoms. Combining this methodology with reversible Michael addition onto nitrostyrenes provides a route to 3‐styrylated BODIPYs. Furthermore, the one‐step, Pd‐catalyzed C–H arylation of 3,5‐unsubstituted BODIPYs leads to 3‐ and 3,5‐arylated dyes. Finally, radical C–H arylation at the 3,5‐positions of α‐unsubstituted BODIPYs provides an additional synthesis route to arylated dyes.

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Section: Functionalization At the 3‐ And 35‐positionsmentioning

confidence: 99%

Postfunctionalization of the BODIPY Core: Synthesis and Spectroscopy

2015

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“…Quinolines 1a-f and solvents were purchased from commercial sources and used without further purification. Samples of acylacetylenes 2a-f , i [ 38 ] and 2g , h [ 39 ], were obtained according to describe methods. Monitoring of the reaction was carried out using the method of IR spectroscopy to follow the disappearance of the C C bond intensity of acetylenes 2 at 2195-2264 cm −1 .…”

Section: Methodsmentioning

confidence: 99%

Acylacetylenes in multiple functionalization of hydroxyquinolines and quinolones

et al. 2020

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The expected one-pot multiple functionalization of hydroxyquinolines and quinolones with acylacetylenes (20 mol% KOH, 5 equiv. H 2 O, MeCN, 55–60 °C), which, according to the previous finding, might involve the addition of OH and NH-functions to the triple bond and insertion of acylacetylenes into the quinoline scaffold, retains mainly on the formation of chalcone-quinoline ensembles in up 99% yield. The higher functionalized quinolines can be obtained in a synthetically acceptable yield, when the above ensembles are treated with the second molecule of acylacetylenes. Thus, the further insertion of second molecule of the acetylenes into the quinoline scaffold occurs as a much slower process indicating a strong adverse substituent effect of the remote chalcone moiety.

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“…This methodology was already partially documented in recent reviews [44][45][46][47][48][49][50][51][52]. This survey covers the recent publications (since 2014) concerning this reaction and the related chemistry which have not been yet summarized in a review.…”

Section: Introductionmentioning

confidence: 97%

Recent Strides in the Transition Metal-Free Cross-Coupling of Haloacetylenes with Electron-Rich Heterocycles in Solid Media

Собенина

Трофимов

2020

Molecules

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The publications covering new, transition metal-free cross-coupling reactions of pyrroles with electrophilic haloacetylenes in solid medium of metal oxides and salts to regioselectively afford 2-ethynylpyrroles are discussed. The reactions proceed at room temperature without catalyst and base under solvent-free conditions. These ethynylation reactions seem to be particularly important, since the common Sonogashira coupling does not allow ethynylpyrroles with strong electron-withdrawing substituents at the acetylenic fragments to be synthesized. The results on the behavior of furans, thiophenes, and pyrazoles under the conditions of these reactions are also provided. The reactivity and structural peculiarities of nucleophilic addition to the activated acetylene moiety of the novel C-ethynylpyrroles are considered.

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Pyrroles and N-Vinylpyrroles from Ketones and Acetylenes

Cited by 54 publications

References 134 publications

Postfunctionalization of the BODIPY Core: Synthesis and Spectroscopy

Postfunctionalization of the BODIPY Core: Synthesis and Spectroscopy

Acylacetylenes in multiple functionalization of hydroxyquinolines and quinolones

Recent Strides in the Transition Metal-Free Cross-Coupling of Haloacetylenes with Electron-Rich Heterocycles in Solid Media

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