A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments
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 phototrans...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2022-05-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.18.61 |
| _version_ | 1811244056262475776 |
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| author | Constantine V. Milyutin Andrey N. Komogortsev Boris V. Lichitsky Valeriya G. Melekhina |
| author_facet | Constantine V. Milyutin Andrey N. Komogortsev Boris V. Lichitsky Valeriya G. Melekhina |
| author_sort | Constantine V. Milyutin |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-12T14:18:06Z |
| format | Article |
| id | doaj.art-f7eaa1f89e844102a6e24fb19dfeb4c2 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-04-12T14:18:06Z |
| publishDate | 2022-05-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-f7eaa1f89e844102a6e24fb19dfeb4c22022-12-22T03:29:39ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-05-0118158859610.3762/bjoc.18.611860-5397-18-61A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragmentsConstantine V. Milyutin0Andrey N. Komogortsev1Boris V. Lichitsky2Valeriya G. Melekhina3N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow 119991, Russian Federation N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow 119991, Russian Federation N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow 119991, Russian Federation N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow 119991, Russian Federation 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.https://doi.org/10.3762/bjoc.18.61allomaltolesipt processphotochemistrypyrazolesterarylenes |
| spellingShingle | Constantine V. Milyutin Andrey N. Komogortsev Boris V. Lichitsky Valeriya G. Melekhina A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments Beilstein Journal of Organic Chemistry allomaltol esipt process photochemistry pyrazoles terarylenes |
| title | A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments |
| title_full | A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments |
| title_fullStr | A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments |
| title_full_unstemmed | A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments |
| title_short | A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments |
| title_sort | study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments |
| topic | allomaltol esipt process photochemistry pyrazoles terarylenes |
| url | https://doi.org/10.3762/bjoc.18.61 |
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