Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates
A straightforward synthetic protocol for the efficient construction of diazepine-containing spiroindolines has been developed and proceeds through a by base-promoted annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates. The reaction mechanism of this formal [4 + 3]...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2023-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.19.143 |
| _version_ | 1797323444395704320 |
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| author | Xing Liu Wenjing Shi Jing Sun Chao-Guo Yan |
| author_facet | Xing Liu Wenjing Shi Jing Sun Chao-Guo Yan |
| author_sort | Xing Liu |
| collection | DOAJ |
| description | A straightforward synthetic protocol for the efficient construction of diazepine-containing spiroindolines has been developed and proceeds through a by base-promoted annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates. The reaction mechanism of this formal [4 + 3] annulation includes the in situ generated allylic ylide, nucleophilic substitution, Michael additon, and elimination processes. Additionally, the similar reaction with α-halogenated N-tosylhydrazones also afforded N-tosyl-substituted spiro[indoline-3,5'-[1,2]diazepine] in satisfactory yields. This protocol provides a convenient approach for the assembly of diverse highly functionalized spiro[indoline-3,5'-[1,2]diazepines] and also features a broad substrate scope, simple reaction conditions, and high molecular convergence. |
| first_indexed | 2024-03-08T05:28:46Z |
| format | Article |
| id | doaj.art-3a3601cc6f4f4304b4f956fffd4ed997 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-03-08T05:28:46Z |
| publishDate | 2023-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-3a3601cc6f4f4304b4f956fffd4ed9972024-02-06T09:08:29ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972023-12-011911923193210.3762/bjoc.19.1431860-5397-19-143Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonatesXing Liu0Wenjing Shi1Jing Sun2Chao-Guo Yan3College of Chemistry & Chemical Engineering, Yangzhou University, Jiangsu, Yangzhou 225002, China College of Chemistry & Chemical Engineering, Yangzhou University, Jiangsu, Yangzhou 225002, China College of Chemistry & Chemical Engineering, Yangzhou University, Jiangsu, Yangzhou 225002, China College of Chemistry & Chemical Engineering, Yangzhou University, Jiangsu, Yangzhou 225002, China A straightforward synthetic protocol for the efficient construction of diazepine-containing spiroindolines has been developed and proceeds through a by base-promoted annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates. The reaction mechanism of this formal [4 + 3] annulation includes the in situ generated allylic ylide, nucleophilic substitution, Michael additon, and elimination processes. Additionally, the similar reaction with α-halogenated N-tosylhydrazones also afforded N-tosyl-substituted spiro[indoline-3,5'-[1,2]diazepine] in satisfactory yields. This protocol provides a convenient approach for the assembly of diverse highly functionalized spiro[indoline-3,5'-[1,2]diazepines] and also features a broad substrate scope, simple reaction conditions, and high molecular convergence.https://doi.org/10.3762/bjoc.19.143acylhydrazoneannulationazepinembh carbonatespirooxindole |
| spellingShingle | Xing Liu Wenjing Shi Jing Sun Chao-Guo Yan Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates Beilstein Journal of Organic Chemistry acylhydrazone annulation azepine mbh carbonate spirooxindole |
| title | Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates |
| title_full | Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates |
| title_fullStr | Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates |
| title_full_unstemmed | Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates |
| title_short | Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates |
| title_sort | construction of diazepine containing spiroindolines via annulation reaction of α halogenated n acylhydrazones and isatin derived mbh carbonates |
| topic | acylhydrazone annulation azepine mbh carbonate spirooxindole |
| url | https://doi.org/10.3762/bjoc.19.143 |
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