Synthesis of a Novel Tetracyclic Isoxazole by Intramolecular Nitrile Oxide Cycloaddition
Intramolecular cycloadditions have the great advantage of forming two rings simultaneously. We report the use of intramolecular [3 + 2] cycloaddition of the nitrile oxide derived from an <i>N</i>-propargylbenzimidazole oxime in the synthesis of a hitherto unreported tetracyclic isoxazole...
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| Format: | Article |
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MDPI AG
2024-02-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2024/1/M1767 |
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| author | Gavin R. Hoffman Allen M. Schoffstall |
| author_facet | Gavin R. Hoffman Allen M. Schoffstall |
| author_sort | Gavin R. Hoffman |
| collection | DOAJ |
| description | Intramolecular cycloadditions have the great advantage of forming two rings simultaneously. We report the use of intramolecular [3 + 2] cycloaddition of the nitrile oxide derived from an <i>N</i>-propargylbenzimidazole oxime in the synthesis of a hitherto unreported tetracyclic isoxazole-containing ring system bearing “6-5-5-5”-membered ring fusions. The initial condensation was achieved through reaction of <i>o</i>-phenylenediamine with ethyl diethoxyacetate, followed by alkylation with propargyl bromide, deprotection of the acetal to the aldehyde, formation of an aldoxime, and intramolecular nitrile oxide cycloaddition (INOC). Characterization of the aldoxime and tetracyclic isoxazole is included herein. |
| first_indexed | 2024-04-24T17:59:00Z |
| format | Article |
| id | doaj.art-19c22dc212344ee58477b13a288330c8 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-04-24T17:59:00Z |
| publishDate | 2024-02-01 |
| publisher | MDPI AG |
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| series | Molbank |
| spelling | doaj.art-19c22dc212344ee58477b13a288330c82024-03-27T13:56:36ZengMDPI AGMolbank1422-85992024-02-0120241M176710.3390/M1767Synthesis of a Novel Tetracyclic Isoxazole by Intramolecular Nitrile Oxide CycloadditionGavin R. Hoffman0Allen M. Schoffstall1Department of Chemistry and Biochemistry, University of Colorado Colorado Springs, Colorado Springs, CO 80918, USADepartment of Chemistry and Biochemistry, University of Colorado Colorado Springs, Colorado Springs, CO 80918, USAIntramolecular cycloadditions have the great advantage of forming two rings simultaneously. We report the use of intramolecular [3 + 2] cycloaddition of the nitrile oxide derived from an <i>N</i>-propargylbenzimidazole oxime in the synthesis of a hitherto unreported tetracyclic isoxazole-containing ring system bearing “6-5-5-5”-membered ring fusions. The initial condensation was achieved through reaction of <i>o</i>-phenylenediamine with ethyl diethoxyacetate, followed by alkylation with propargyl bromide, deprotection of the acetal to the aldehyde, formation of an aldoxime, and intramolecular nitrile oxide cycloaddition (INOC). Characterization of the aldoxime and tetracyclic isoxazole is included herein.https://www.mdpi.com/1422-8599/2024/1/M1767isoxazoletetracyclenitrile oxideintramolecular cycloadditionclick chemistry |
| spellingShingle | Gavin R. Hoffman Allen M. Schoffstall Synthesis of a Novel Tetracyclic Isoxazole by Intramolecular Nitrile Oxide Cycloaddition Molbank isoxazole tetracycle nitrile oxide intramolecular cycloaddition click chemistry |
| title | Synthesis of a Novel Tetracyclic Isoxazole by Intramolecular Nitrile Oxide Cycloaddition |
| title_full | Synthesis of a Novel Tetracyclic Isoxazole by Intramolecular Nitrile Oxide Cycloaddition |
| title_fullStr | Synthesis of a Novel Tetracyclic Isoxazole by Intramolecular Nitrile Oxide Cycloaddition |
| title_full_unstemmed | Synthesis of a Novel Tetracyclic Isoxazole by Intramolecular Nitrile Oxide Cycloaddition |
| title_short | Synthesis of a Novel Tetracyclic Isoxazole by Intramolecular Nitrile Oxide Cycloaddition |
| title_sort | synthesis of a novel tetracyclic isoxazole by intramolecular nitrile oxide cycloaddition |
| topic | isoxazole tetracycle nitrile oxide intramolecular cycloaddition click chemistry |
| url | https://www.mdpi.com/1422-8599/2024/1/M1767 |
| work_keys_str_mv | AT gavinrhoffman synthesisofanoveltetracyclicisoxazolebyintramolecularnitrileoxidecycloaddition AT allenmschoffstall synthesisofanoveltetracyclicisoxazolebyintramolecularnitrileoxidecycloaddition |