Synthesis and photophysical properties of novel multisubstituted benzene and naphthalene derivatives with high 2D-π-conjugation

Kula, Sławomir; Szłapa, Agata; Małecki, Jan Grzegorz; Maroń, Anna; Matussek, Marek; Schab‐Balcerzak, Ewa; Siwy, Mariola; Domański, Marian; Sojka, Maciej; Danikiewicz, Witold; Krompiec, Stanisław; Filapek, Michał

doi:10.1016/j.optmat.2015.07.011

Cited by 12 publications

(7 citation statements)

References 55 publications

(77 reference statements)

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“…In 2015, Kula with colleagues reported that a small molecule with D-A-D framework was prepared using a [2 + 1 + 2 + 1] cycloaddition (providing 2-pyranones) followed by the [4 + 2] Diels–Alders reaction with CO 2 extrusion ( Scheme 246 ) [ 304 ].…”

Section: 2-pyranones For the Multisubstituted Benzene Ring And Naphthalene System Formation/creationmentioning

confidence: 99%

“…In 2015, Kula et al, reported synthesising tetra-substituted naphthalene derivatives via DA cycloaddition of in situ generated benzyne to 2-pyranones ( Scheme 256 ) [ 304 ].…”

Section: 2-pyranones For the Multisubstituted Benzene Ring And Naphthalene System Formation/creationmentioning

confidence: 99%

“…The influence of this type of interaction on photophysical properties with the aid of DFT calculations was examined. The preliminary tests of the application possibility of synthesised compounds in devices for optoelectronics were optimistic [ 304 ].…”

Section: 2-pyranones For the Multisubstituted Benzene Ring And Naphthalene System Formation/creationmentioning

confidence: 99%

“… Acetylenedicarboxylate DA cycloaddition to in situ prepared 2-pyranones [ 304 ]. Reagents and conditions: R 1 = Me or n -Pr, R 2 = H, Me or Bn, Ar = Ph or 2,2′-bitiophen-5-yl; a = [ReBr(CO) 3 (thf)] 2 , MS4A, 180 °C, 24 h; b = 150 °C, 24 h, up to 60% yield.…”

Section: Figure and Schemesmentioning

confidence: 99%

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Diels–Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry

et al. 2021

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Phenyl, naphthyl, polyarylphenyl, coronene, and other aromatic and polyaromatic moieties primarily influence the final materials’ properties. One of the synthetic tools used to implement (hetero)aromatic moieties into final structures is Diels–Alder cycloaddition (DAC), typically combined with Scholl dehydrocondensation. Substituted 2-pyranones, 1,1-dioxothiophenes, and, especially, 1,3-cyclopentadienones are valuable substrates for [4 + 2] cycloaddition, leading to multisubstituted derivatives of benzene, naphthalene, and other aromatics. Cycloadditions of dienes can be carried out with extrusion of carbon dioxide, carbon oxide, or sulphur dioxide. When pyranones, dioxothiophenes, or cyclopentadienones and DA cycloaddition are aided with acetylenes including masked ones, conjugated or isolated diynes, or polyynes and arynes, aromatic systems are obtained. This review covers the development and the current state of knowledge regarding thermal DA cycloaddition of dienes mentioned above and dienophiles leading to (hetero)aromatics via CO, CO2, or SO2 extrusion. Particular attention was paid to the role that introduced aromatic moieties play in designing molecular structures with expected properties. Undoubtedly, the DAC variants described in this review, combined with other modern synthetic tools, constitute a convenient and efficient way of obtaining functionalized nanomaterials, continually showing the potential to impact materials sciences and new technologies in the nearest future.

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Section: 2-pyranones For the Multisubstituted Benzene Ring And Naphthalene System Formation/creationmentioning

confidence: 99%

“…In 2015, Kula et al, reported synthesising tetra-substituted naphthalene derivatives via DA cycloaddition of in situ generated benzyne to 2-pyranones ( Scheme 256 ) [ 304 ].…”

Section: 2-pyranones For the Multisubstituted Benzene Ring And Naphthalene System Formation/creationmentioning

confidence: 99%

Section: 2-pyranones For the Multisubstituted Benzene Ring And Naphthalene System Formation/creationmentioning

confidence: 99%

Section: Figure and Schemesmentioning

confidence: 99%

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Diels–Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry

et al. 2021

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“…1, and distribution diagrams of its species would provide the knowledge about the extent to establish the proper ionization state of compound (also considered as potent drug or pro-drug) presents at physiological pH. Electrochemistry of carbazole compounds is an object of interest mainly because of their applications [19][20][21][22][23] . However, it has been shown that the mechanism of biological action of some biologically active compounds is associated with their redox activity 24,25 .…”

mentioning

confidence: 99%

Photosensitive and pH-dependent activity of pyrazine-functionalized carbazole derivative as promising antifungal and imaging agent

Chylewska

Dąbrowska

Ramotowska

et al. 2020

Sci Rep

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Carbazole skeleton plays a significant role as a structural scaffold of many pharmacologically active compounds. Pyrazine-functionalized carbazole derivative was constructed by coupling 2-amino-5-bromo-3-methylaminepyrazine (ABMAP) into 3 and 6 positions of the carbazole ring. Multiexperimental methods were used, e.g., potentiometric, spectroscopic (ATR, UV, XRD powder, 1 H and 13 C NMR), electrochemical (cyclic voltammetry), and optical techniques, to receive the complete structural analysis, physicochemical (pKa, logP) and biological profile of a new carbazole derivative with acronym 3,6-PIRAMICAR. the interaction ability of the compound studied with potential cellular targets like Calf Thymus DNA (CT-DNA), or BovineSerumAlbumin (BSA) were also taken into account. experiments showed the existence of strong binding, but no DnA or BSA cleavage was observed. the comparative analyzes of compounds anti-Candida action clearly show pH-dependent antifungal activity of 3,6-PIRAMICAR , which was strongly stimulated in the acidic media. Surprisingly, the titled compound turn out to be much more effective (14 times by MIC50; 8 times by MIC; c.a. 4 times by MFC) against Candidakrusei than fluconazole at pH 4. The emergence of multidrug-resistant microorganisms, as well as fungal infectious diseases, is a major global problem, especially for immuno-deficient populations. The development of new antifungal agents in clinical trials is problematic inferior to the incidence of drug resistance, and the available antifungal agents are restricted. Their mechanisms are based on certain characteristics of the fungus in order to avoid biological similarities with the host 1. Fungi in the Candida genus are the most common fungal pathogens which can colonize various host niches (stomach, vagina and oral mucosa) with varying ambient pH range 2-6. Carbazoles and derivatives with carbazole skeleton are currently tested intensively according to their antimicrobial properties which is directly relating with their structure or in more details with anaromatic N-heterocyclic ring inside 7. Carbazole derivatives have been reported to be potential agents against tumor 8 or opportunistic infections of AIDS 9,10. The studies about high active DNA intercalators show the significance of the carbazole structural agents like planarity or aromaticity 11,12. Interestingly, the mentioned parameters are described as responsible for the high affinity of carbazoles substituted at 3,6-or 2,7-positions by amine, amidine, or imidazoline groups to GC or AT-rich sequences of DNA 13,14. However, chemistry of especially di-substituted 3,6-derivatives of carbazole is still not very extensively explored due to problems with synthesis of such compounds. Mainly nitrogen atom was a hot spot for carbazole derivatives 14. The first concept of the studies was to check the basic design structures assumptions to predict pharmaceuticals activity, like presented carbazole functionalized by pyrazines-our previous research objects. Consequently, the confirmation of the possibili...

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Triflic‐Acid‐Catalyzed Tandem Epoxide Rearrangement and Annulation with Alkynes: An Efficient Approach for Regioselective Synthesis of Naphthalenes

Rao¹,

Sudheer²,

Battula³

2022

ChemistrySelect

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A facile triflic acid catalyzed method to synthesize 1-arylnaphthalenes from one-pot annulation reaction of arylepoxides and arylalkynes has been reported. The annulation reaction involves a successive epoxide to carbonyl rearrangement, electrophilic attack of carbonyl on arylalkyne followed by cyclization catalyzed by triflic acid. The present catalyst effects this transformation at room temperature itself.

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Synthesis and photophysical properties of novel multisubstituted benzene and naphthalene derivatives with high 2D-π-conjugation

Cited by 12 publications

References 55 publications

Diels–Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry

Diels–Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry

Photosensitive and pH-dependent activity of pyrazine-functionalized carbazole derivative as promising antifungal and imaging agent

Triflic‐Acid‐Catalyzed Tandem Epoxide Rearrangement and Annulation with Alkynes: An Efficient Approach for Regioselective Synthesis of Naphthalenes

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