Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles
For the first time, the reaction of substituted 2H-furo[3,2-b]pyran-2-ones with diverse N-nucleophiles was investigated. It was shown that the direction of the process depends on the type of employed nitrogen-containing reagent. For example, condensation with aliphatic amines leads to 2H-furo[3,2-b]...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2025-03-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.21.44 |
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| author | Constantine V. Milyutin Andrey N. Komogortsev Boris V. Lichitsky |
| author_facet | Constantine V. Milyutin Andrey N. Komogortsev Boris V. Lichitsky |
| author_sort | Constantine V. Milyutin |
| collection | DOAJ |
| description | For the first time, the reaction of substituted 2H-furo[3,2-b]pyran-2-ones with diverse N-nucleophiles was investigated. It was shown that the direction of the process depends on the type of employed nitrogen-containing reagent. For example, condensation with aliphatic amines leads to 2H-furo[3,2-b]pyran-2,7(3H)-diones bearing an exocyclic enamine moiety. At the same time, interaction with dinucleophiles results in recyclization accompanied by opening of the furan ring. Relied on the aforementioned process a general method for the synthesis of substituted pyrazol-3-ones with allomaltol fragment was designed. Structures of representatives of all obtained products were unambiguously confirmed by X-ray diffraction. |
| format | Article |
| id | doaj-art-9f776ddecece4b8f8625db439049ecda |
| institution | OA Journals |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-9f776ddecece4b8f8625db439049ecda2025-08-20T02:08:15ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-03-0121155656310.3762/bjoc.21.441860-5397-21-44Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophilesConstantine V. Milyutin0Andrey N. Komogortsev1Boris V. Lichitsky2N.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 For the first time, the reaction of substituted 2H-furo[3,2-b]pyran-2-ones with diverse N-nucleophiles was investigated. It was shown that the direction of the process depends on the type of employed nitrogen-containing reagent. For example, condensation with aliphatic amines leads to 2H-furo[3,2-b]pyran-2,7(3H)-diones bearing an exocyclic enamine moiety. At the same time, interaction with dinucleophiles results in recyclization accompanied by opening of the furan ring. Relied on the aforementioned process a general method for the synthesis of substituted pyrazol-3-ones with allomaltol fragment was designed. Structures of representatives of all obtained products were unambiguously confirmed by X-ray diffraction.https://doi.org/10.3762/bjoc.21.44allomaltolenamines2h-furo[3,2-b]pyran-2-onespyrazol-3-onesrecyclization |
| spellingShingle | Constantine V. Milyutin Andrey N. Komogortsev Boris V. Lichitsky Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles Beilstein Journal of Organic Chemistry allomaltol enamines 2h-furo[3,2-b]pyran-2-ones pyrazol-3-ones recyclization |
| title | Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles |
| title_full | Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles |
| title_fullStr | Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles |
| title_full_unstemmed | Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles |
| title_short | Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles |
| title_sort | study of the interaction of 2h furo 3 2 b pyran 2 ones with nitrogen containing nucleophiles |
| topic | allomaltol enamines 2h-furo[3,2-b]pyran-2-ones pyrazol-3-ones recyclization |
| url | https://doi.org/10.3762/bjoc.21.44 |
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