Ultraviolet irradiation of terarylenes: A facile, efficient, and environmentally friendly method for the synthesis of fused polycyclic products

Melekhina, Valeriya G.; Mityanov, Vitaly S.; Lichitsky, Boris V.; Komogortsev, Andrey N.; Фахрутдинов, Артем Н.; Даева, Е. Д.; Krayushkin, М. М.

doi:10.1016/j.tetlet.2019.05.063

Cited by 19 publications

(13 citation statements)

References 20 publications

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“…Recently, an efficient photocyclization of close analogs of compounds 1 a towards naphtho[1′,2′:4,5]imidazo[1,2‐ a ]pyridine derivatives was reported [30,38] . However, the corresponding substrates did not contain a DAE moiety, so their cyclization in VBA mode was non‐alternative.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, an efficient photocyclization of close analogs of compounds 1 a towards naphtho[1',2':4,5]imidazo[1,2-a]pyridine derivatives was reported. [30,38] However, the corresponding substrates did not contain a DAE moiety, so their cyclization in VBA mode was non-alternative. In our case, the VBA-type cyclization turned out to be the dominant process and no even traces of products 2 were observed.…”

Section: Resultsmentioning

confidence: 99%

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Competition between Two Modes of 6π‐Photocyclization: A Case Study for 3‐(1,2‐Diarylvinyl)‐2‐arylimidazo[1,2‐a]pyridines

et al. 2022

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The photochemical 6π‐electrocyclization of diarylethenes (DAE), 2‐vinylbiaryls (VBA) and their derivatives is widely used in organic synthesis. Combination of these motifs in one molecule opens the issue of selectivity of the photochemical reaction. We have found that upon UV irradiation, 3‐(1,2‐diarylvinyl)‐2‐arylimidazo[1,2‐a]pyridines comprising both DAE and VBA moieties form products of VBA cyclization followed by oxidation. The selectivity of the process was rationalized by DFT calculations. The presented reaction gave access to highly fluorescent 5,6‐diarylnaphtho[1′,2′:4,5]imidazo[1,2‐a]pyridine derivatives.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Competition between Two Modes of 6π‐Photocyclization: A Case Study for 3‐(1,2‐Diarylvinyl)‐2‐arylimidazo[1,2‐a]pyridines

et al. 2022

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“…In this case, 1,3,5-hexatriene fragment plays role of photoremovable protective group (PPG). [16] There are some examples of aforementioned processes leading to elimination of water molecule [17][18][19][20] or various alcohols described in the literature. [21,22] Also, photocyclization of 1,3,5-hexatriene systems can be completed by the formation of various acids, for example hydrogen halides, [23,24] sulfonic [25][26][27] or carboxylic acids [25,28] (Scheme 1A).…”

Section: Introductionmentioning

confidence: 99%

Photoinduced 6π‐electrocyclization of 2,5‐dichlorothiophene containing benzofuranylacrylonitriles as efficient method for the generation of hydrogen chloride

Karibov

Lichitsky

Komogortsev

et al. 2022

Journal of Heterocyclic Chem

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The photochemical 6π‐electrocyclization of 1,3,5‐hexatriene system containing benzofuran and 2,5‐dichlorothiophene fragments was investigated. It was shown that considered photoreaction regiospecifically leads to the formation of substituted benzo[b]thieno[2,3‐g]benzofurans. Along with the formation of polyheterocyclic products the studied process is accompanied by the elimination of hydrogen chloride molecule. Based on the suggested transformation an efficient method for the photogeneration of strong acid was implemented. As a result, the starting thienyl substituted benzofurans can be used as photoacid generators (PAGs). The structure of one of the final products was established by X‐ray diffraction.

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“…The efficient preparative method for the synthesis of various polyheterocyclic systems is based on this type of photocyclization. [ 9–14 ] Thus, the development of new approaches to the synthesis of 1,3,5‐hexatriene systems containing an enol fragment is an actual task. A convenient approach to the synthesis of hydroxyl‐containing terarylenes is based on the application of the multicomponent reactions (MCRs) methodology.…”

Section: Introductionmentioning

confidence: 99%

Multicomponent one‐pot synthesis of novel imidazole‐2‐thione derivatives containing allomaltol fragment

Komogortsev

Melekhina

Lichitsky

et al. 2021

Journal of Heterocyclic Chem

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A convenient method for the synthesis of novel imidazole‐2‐thione derivatives containing allomaltol fragment was elaborated. This approach includes one‐pot multicomponent reaction of allomaltol, arylglyoxals, primary amines followed by addition of alkyl or aryl isothiocyanates. It was shown that the key intermediates of the studied process are substituted α‐aminoketones and the corresponding imidazolidine‐2‐thione. The advantages of this synthesis are mild reaction conditions, atom economy, and easy workup procedure, which can avoid chromatographic purifications. The structures of an intermediate imidazolidine‐2‐thione and one of the final imidazole‐2‐thiones were determined by X‐ray diffraction.

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Ultraviolet irradiation of terarylenes: A facile, efficient, and environmentally friendly method for the synthesis of fused polycyclic products

Cited by 19 publications

References 20 publications

Competition between Two Modes of 6π‐Photocyclization: A Case Study for 3‐(1,2‐Diarylvinyl)‐2‐arylimidazo[1,2‐a]pyridines

Competition between Two Modes of 6π‐Photocyclization: A Case Study for 3‐(1,2‐Diarylvinyl)‐2‐arylimidazo[1,2‐a]pyridines

Photoinduced 6π‐electrocyclization of 2,5‐dichlorothiophene containing benzofuranylacrylonitriles as efficient method for the generation of hydrogen chloride

Multicomponent one‐pot synthesis of novel imidazole‐2‐thione derivatives containing allomaltol fragment

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