The synthesis of new pyrrolo[1,2-a]perimidin-10-one dyes via two convenient routes and its characterizations

Koca, İrfan; Üngören, Şevket Hakan; Kıbrız, İbrahim Evren; Yılmaz, Filiz

doi:10.1016/j.dyepig.2012.04.016

Cited by 20 publications

(15 citation statements)

References 19 publications

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“…The stretching vibrations band of the bound amino group NH is observed at 3364-3440 cm -1 , the broadened stretching vibrations band of bound hydroxy groups ОН that appear commonly in the same region in the IR spectra of cyclic isomers are absent from the spectra of compounds 2с and 3с. 1 Н NMR spectra of compounds 2с and 3с contain broadened singlets from the protons of the amide amino group at 7.70-7.71 ppm (1Н) and from protons of the primary amino groups at 3.95 (2Н, 2с) and 5.52 (2Н, 3с) ppm, the values close to those of signals of unsubstituted amino groups of isomeric phenylenediamines and benzidine respectively. Consequently, the effect of the fragments of 4-aryl-4-oxocarboxylic acids on shielding the protons of primary amino groups is insignificant.…”

mentioning

confidence: 80%

“…IR spectrum, ν, cm -1 : 3380 (NH 2 ), 1698 (С=О, amide-I). 1 Compounds 4b-4d and 5c were similarly prepared. …”

Section: -(3-aminophenyl)-5-octyl-13-dihydro-2н-pyrrol-2-one (4а)mentioning

confidence: 99%

“…The refinement of pyrrole preparation procedures is very important for organic chemistry since the pyrrole ring is present in the structure of many substances both of biologic origin (vitamin B 12 , prodigiosin pigment) and purposefully synthesized in a laboratory (for instance, fluorescent dyes of BODIPY class) [1].…”

mentioning

confidence: 99%

“…Pyrrolidones of more complex structure [1] were obtained in over 80% yield in reactions of heterocyclic ketene aminals containing a perimidine fragment with oxalyl chloride in acetonitrile. Compounds of this series significantly differing by electron absorption spectra can exist in three tautomeric forms (enol-imine, keto-amine, and keto-imine).…”

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confidence: 99%

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Synthesis of 1-substituted 5-alkyl(aryl)-1,3-dihydro-2H-pyrrol-2-ones. Azocoupling with diazonium salts

2016

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Reactions of 5-alkyl-and 5-aryl-3H-furan-2-ones with 1,3-and 1,4-binucleophiles of aromatic series were carried out for the first time under various conditions. In the presence of a base the reaction resulted in 1-R-1,3-dihydro-2Н-pyrrol-2-ones, under milder conditions intermediates were isolated, 4-aryl-4oxobutanamides. The structure of the latter was proved by spectral methods. By an example of 1-R-1,3dihydro-2Н-pyrrol-2-ones the possibility was demonstrated of their functionalization via introducing an aryldiazenyl fragment.

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mentioning

confidence: 80%

“…IR spectrum, ν, cm -1 : 3380 (NH 2 ), 1698 (С=О, amide-I). 1 Compounds 4b-4d and 5c were similarly prepared. …”

Section: -(3-aminophenyl)-5-octyl-13-dihydro-2н-pyrrol-2-one (4а)mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis of 1-substituted 5-alkyl(aryl)-1,3-dihydro-2H-pyrrol-2-ones. Azocoupling with diazonium salts

2016

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“…The pyrrolopyrimidine is an important class of N ‐heterocyclic compounds which has displayed various biological activities such as antibacterial, anti‐HIV type, anti‐microbial, anti‐fungal, anti‐viral, antitumor, and antiinflammatory, properties. In addition, pyrrolo[1,2‐ a ]pyrimidine framework is an important structural part of some pigments and dyes for plastics . Furthermore, compounds containing 1,3‐indandione skeleton have peculiar biological and medicinal properties…”

Section: Introductionmentioning

confidence: 99%

A Highly Efficient Synthesis of Pyrrolo[1,2‐a]pyrimidine Derivatives Containing 1,3‐Indandione Skeleton

2019

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The pyrimidines fused with pyrrole ring, pyrrolopyrimidines, showed broad applicability in medicinal chemistry. Herein, we synthesized the new derivatives (8 examples) of pyrrolo[1,2-a] pyrimidine containing 1,3-indandione skeleton by the use of triethylammonium thiolates, methyl iodide, and ketene aminals via a one-pot three-component reaction. Scheme 1. Synthesis of pyrrolo[1,2-a]pyrimidine containing 1,3-indandione skeleton.

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Synthesis, Characterization, and Spectroscopic Properties of Allylic Ruthenium(II) Complexes of a Highly Conjugated Perinone

et al. 2019

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Highly conjugated perinones were evaluated as proligands with [Ru(η 6 -arene)Cl 2 ] 2 precursors (arene = p-cymene or benzene). None of them, except itaco-perinone (IP) bearing one exocyclic methylene group, were able to form coordination compounds. Expected η 1 -coordination through the lone pair of the nitrogen or oxygen atoms of the perinone did not occur. Instead a deprotonation reaction involving the exocyclic methylene was observed and the corresponding [Ru(η 6 -arene)- [a] 3494 (η 3 -IP)Cl] complex was isolated in moderate yields. Mechanistic studies revealed that the base-promoted isomerization of itacoperinone to citraco-perinone prevented higher yields in the synthesis of the allylic complexes. Additionally, it was observed that IP can dimerize through the exocyclic methylene group, indicating high reactivity of this carbon-carbon double bond. Electronic absorption and emission properties of the perinones and organometallic compounds were studied.

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The synthesis of new pyrrolo[1,2-a]perimidin-10-one dyes via two convenient routes and its characterizations

Cited by 20 publications

References 19 publications

Synthesis of 1-substituted 5-alkyl(aryl)-1,3-dihydro-2H-pyrrol-2-ones. Azocoupling with diazonium salts

Synthesis of 1-substituted 5-alkyl(aryl)-1,3-dihydro-2H-pyrrol-2-ones. Azocoupling with diazonium salts

A Highly Efficient Synthesis of Pyrrolo[1,2‐a]pyrimidine Derivatives Containing 1,3‐Indandione Skeleton

Synthesis, Characterization, and Spectroscopic Properties of Allylic Ruthenium(II) Complexes of a Highly Conjugated Perinone

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