From acylethynylpyrroles to pyrrole-pyrone ensembles in a one step

Gotsko, Maxim D.; Saliy, Ivan V.; Собенина, Л. Н.; Ushakov, Igor А.; Трофимов, Б. А.

doi:10.1016/j.tetlet.2019.151126

Cited by 9 publications

(4 citation statements)

References 29 publications

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“…2-Acylethynylpyrroles 1a,f – l,n – r were obtained from pyrroles and 2-acylbromoacetylenes accordingly to methodology [ 40 , 41 , 42 ]. Physico-chemical characteristics 2-acylethynylpyrroles 1a,f – l,n – r were given in [ 40 , 43 , 44 , 45 , 46 , 47 ]. 2-Acylethynylpyrroles 1b,c – e,m,s – v were obtained accordingly to the following procedure:…”

Section: Methodsmentioning

confidence: 99%

“…Acylethynylpyrroles 1a,f-l,n-r were obtained from pyrroles and 2-acylbromoacetylenes accordingly to methodology[40][41][42]. Physico-chemical characteristics 2-acylethynylpyrroles 1a,f-l,n-r were given in[40,[43][44][45][46][47]. 2-Acylethynylpyrroles 1b,c-e,m,s-v were obtained accordingly to the following procedure:The corresponding pyrrole (1 mmol) and acyl(bromo)acetylene (1 mmol) were carefully ground in a porcelain mortar with alumina [10-fold amount by weight of combined mass of pyrrole and acyl(bromo)acetylene] at 20-25 • C for 5 min.…”

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confidence: 99%

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Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles

et al. 2021

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An efficient method for the synthesis of pharmaceutically prospective pyrrole–aminopyrimidine ensembles (in up to 91% yield) by the cyclocondensation of easily available acylethynylpyrroles with guanidine nitrate has been developed. The reaction proceeds under heating (110–115 °C, 4 h) in the KOH/DMSO system. In the case of 2-benzoylethynylpyrrole, the unexpected addition of the formed pyrrole–aminopyrimidine as N- (NH moiety of the pyrrole ring) and C- (CH of aminopyrimidine) nucleophiles to the triple bond is observed.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles

et al. 2021

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“…The [4+2]-cycloaddition between 2-acylethynylpyrroles 83 and methylene active esters (Scheme 46), offering a short-cut to pyrrolyl pyrones 84 in good to high yields, was described [84]. The reaction was carried out in acetonitrile in the presence of 1.5 molar excess of KOH.…”

Section: Cyclization With Methylene Active Esters: Synthesis Of Pyrromentioning

confidence: 99%

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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“…After the pioneering work, 1,2 which showed that pyrroles are cross-coupled with electrophilic acylhaloacetylenes under exceptionally mild conditions (room temperature) in the solid metal oxides and salts media to give 2-acylethynylpyrroles, this methodology has been developed into a general and efficient tool for the synthesis of diverse alkyl-, aryl-, hetaryl-, cycloalkyl-2ethynylpyrroles, having acyl, 3e5 trifluoroacyl, 6,7 ester, 8,9 aldehyde, 10 phosphonate, 11 ethynyl, 12 and butadiynyl 13 functions at the triple bond.…”

Section: Introductionmentioning

confidence: 99%

Transition metal-free cross-coupling of furan ring with haloacetylenes

et al. 2018

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a b s t r a c tOn the example of menthofuran, a naturally abundant compound, it has been shown for the first time that the furan ring can be readily cross-coupled with acylhaloacetylenes in the solid Al 2 O 3 powder at room temperature to afford the corresponding 2-ethynyl derivatives in up to 88% yield. The reaction represents a ring closing/ring opening process that includes reversible formation of the intermediate cycloadducts further producing acetylene derivatives with elimination of HHal.

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From acylethynylpyrroles to pyrrole-pyrone ensembles in a one step

Cited by 9 publications

References 29 publications

Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles

Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles

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

Transition metal-free cross-coupling of furan ring with haloacetylenes

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