Photoinduced assembly of the 3,4,4a,7a-tetrahydro-1<i>H</i>-cyclopenta[<i>b</i>]pyridine-2,7-dione core on the basis of allomaltol derivatives

Milyutin, Constantine V.; Galimova, Renata D.; Komogortsev, Andrey N.; Lichitskiĭ, B. V.; Melekhina, Valeriya G.; Migulin, Vasily A.; Фахрутдинов, Артем Н.; Minyaev, Mikhail E.

doi:10.1039/d1ob01871j

Cited by 13 publications

(11 citation statements)

References 40 publications

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“…It should be mentioned that studied photoreaction is similar to the previously published cyclization of 3-hydroxypyran-4-one derivatives containing an amide group. [17] Wherein, the final step in the present communication is different and includes reaction with hydroxyl group leading to the formation of tetrahydrofuran ring.…”

Section: Chemistryselectmentioning

confidence: 98%

“…Further capture of the aforementioned labile intermediates allows the synthesis of diverse heterocyclic systems. It should be noted that such trapping can be carried out either under action of the additional reagents [13,14] or intramolecularly using functional groups of the side chain [15,17] (Scheme 1, A). Earlier we have shown that the ester and amide fragments can be used in this capacity.…”

Section: Introductionmentioning

confidence: 99%

“…Among the wide variety of processes of this type, considerable attention is drawn to the phototransformations of compounds containing an allomaltol fragment. [13][14][15][16][17][18][19][20] In addition, note that the modification of allomaltol using classical synthetic methods opens up access to a wide range of products containing a 3-hydroxypyran-4-one fragment. [21][22][23] Further photochemical transformation of such objects makes it possible to obtain a variety of original products that are inaccessible using other approaches.…”

Section: Introductionmentioning

confidence: 99%

“…Photoinduced reactions of heterocyclic compounds are an important part of organic chemistry. Among the wide variety of processes of this type, considerable attention is drawn to the phototransformations of compounds containing an allomaltol fragment [13–20] . In addition, note that the modification of allomaltol using classical synthetic methods opens up access to a wide range of products containing a 3‐hydroxypyran‐4‐one fragment [21–23] .…”

Section: Introductionmentioning

confidence: 99%

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Photochemical Synthesis of Tetrahydro‐6H‐cyclopenta[b]furan‐6‐ones from Substituted Allomaltols

et al. 2022

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A novel UV‐mediated approach for the synthesis of previously unknown 3a,6a‐dihydroxy‐4‐methyl‐2,3,3a,6a‐tetrahydro‐6H‐cyclopenta[b]furan‐6‐one derivatives from easily accessible substituted allomaltols containing a 2‐aryl‐2‐hydroxyethyl fragment was elaborated. The suggested method is based on the ESIPT‐promoted contraction of a 3‐hydroxy‐4‐pyranone moiety followed by intramolecular trapping of a photogenerated α‐hydroxy‐1,2‐diketone intermediate. For the first time, we have demonstrated that a side chain hydroxyl group can be employed for the concluding cyclization with a labile α‐hydroxy‐1,2‐diketone fragment. The structure of one synthesized photoproduct was determined by X‐ray diffraction.

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Section: Chemistryselectmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Photochemical Synthesis of Tetrahydro‐6H‐cyclopenta[b]furan‐6‐ones from Substituted Allomaltols

et al. 2022

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“…An alternative approach for trapping of such unstable intermediates is the preliminary introduction of functional groups into the 3-hydroxypyran-4-one structure. In this case, the intermediate α-hydroxy-1,2-diketone is captured by intramolecular reaction with an active substituent in the side chain ( Scheme 1B ) [ 24 – 25 ]. Thus, the combination of ESIPT-induced photoreactions of 3-hydroxypyran-4-one derivatives and various trapping methods opens up significant synthetic possibilities.…”

Section: Introductionmentioning

confidence: 99%

A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments

Milyutin¹,

Komogortsev²,

Lichitsky³

et al. 2022

Beilstein J. Org. Chem.

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The photochemical properties behavior of 3-hydroxy-4-pyranone containing terarylenes with a pyrazole bridge fragment were studied. It was shown that UV-induced 6π-electrocyclization of the 1,3,5-hexatriene system was not observed for the considered objects molecules. At the same time, the phototransformation of such systems proceeds exclusively in the direction of the contraction of the pyranone ring leading to unstable α-hydroxydiketones. For the first time the possibility of isolation of the resulting α-hydroxydiketones in pure form was demonstrated. Wherein, it was shown that relatively low stable α-hydroxydiketones can be trapped by reaction with 1,2-phenylenediamine. The general method for the preparation of the corresponding quinoxalines on the basis of the aforementioned condensation was implemented. It was demonstrated that the studied photoreaction does not depend on the type of pyrazole bridge. The structures of three of synthesized products were established by X-ray diffraction.

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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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Photoinduced assembly of the 3,4,4a,7a-tetrahydro-1H-cyclopenta[b]pyridine-2,7-dione core on the basis of allomaltol derivatives

Abstract: A novel photochemical synthetic pathway to various substituted 3,4,4a,7a-tetrahydro-1H-cyclopenta[b]pyridine-2,7-diones based on readily available allomaltol derivatives containing an amide group was developed.

Cited by 13 publications

References 40 publications

Photochemical Synthesis of Tetrahydro‐6H‐cyclopenta[b]furan‐6‐ones from Substituted Allomaltols

Photochemical Synthesis of Tetrahydro‐6H‐cyclopenta[b]furan‐6‐ones from Substituted Allomaltols

A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments

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

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