Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis
A new metal-free one-pot three-component procedure towards fully substituted triazolochromenes has been developed, starting from commercially available materials. Salicylaldehydes and nitroalkenes were reacted under solvent-free conditions, followed by a 1,3-dipolar cycloaddition of the intermediate...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-10-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.246 |
| _version_ | 1818853094564298752 |
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| author | Robby Vroemans Yenthel Verhaegen My Tran Thi Dieu Wim Dehaen |
| author_facet | Robby Vroemans Yenthel Verhaegen My Tran Thi Dieu Wim Dehaen |
| author_sort | Robby Vroemans |
| collection | DOAJ |
| description | A new metal-free one-pot three-component procedure towards fully substituted triazolochromenes has been developed, starting from commercially available materials. Salicylaldehydes and nitroalkenes were reacted under solvent-free conditions, followed by a 1,3-dipolar cycloaddition of the intermediate 3-nitro-2H-chromenes with organic azides in a one-pot two-step sequence. The triazolochromenes were formed with complete regioselectivity and new biologically relevant structures were synthesized via extension of the developed procedure and via postfunctionalization. The mechanochemical synthesis was carried out for several salicylaldehydes and gave a clear improvement in the yield of the corresponding triazolochromenes and consequently showed to be a viable alternative for solid salicylaldehydes. |
| first_indexed | 2024-12-19T07:31:21Z |
| format | Article |
| id | doaj.art-faea84fa890e4a9295abae7451764ce0 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T07:31:21Z |
| publishDate | 2018-10-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-faea84fa890e4a9295abae7451764ce02022-12-21T20:30:41ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-10-011412689269710.3762/bjoc.14.2461860-5397-14-246Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesisRobby Vroemans0Yenthel Verhaegen1My Tran Thi Dieu2Wim Dehaen3Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, BelgiumMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, BelgiumMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, BelgiumMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, BelgiumA new metal-free one-pot three-component procedure towards fully substituted triazolochromenes has been developed, starting from commercially available materials. Salicylaldehydes and nitroalkenes were reacted under solvent-free conditions, followed by a 1,3-dipolar cycloaddition of the intermediate 3-nitro-2H-chromenes with organic azides in a one-pot two-step sequence. The triazolochromenes were formed with complete regioselectivity and new biologically relevant structures were synthesized via extension of the developed procedure and via postfunctionalization. The mechanochemical synthesis was carried out for several salicylaldehydes and gave a clear improvement in the yield of the corresponding triazolochromenes and consequently showed to be a viable alternative for solid salicylaldehydes.https://doi.org/10.3762/bjoc.14.246ball millingmulticomponent reaction3-nitro-2H-chromeneone-pot synthesis1,2,3-triazole |
| spellingShingle | Robby Vroemans Yenthel Verhaegen My Tran Thi Dieu Wim Dehaen Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis Beilstein Journal of Organic Chemistry ball milling multicomponent reaction 3-nitro-2H-chromene one-pot synthesis 1,2,3-triazole |
| title | Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis |
| title_full | Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis |
| title_fullStr | Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis |
| title_full_unstemmed | Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis |
| title_short | Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis |
| title_sort | assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis |
| topic | ball milling multicomponent reaction 3-nitro-2H-chromene one-pot synthesis 1,2,3-triazole |
| url | https://doi.org/10.3762/bjoc.14.246 |
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