Synthesis of Polycyclic Tetrahydroisoquinolines and Tetrahydrobenzo[ d ]azepines from Polymer-Supported Allylglycine.
| Autor: | Králová P; Department of Organic Chemistry, Faculty of Science, Palacký University, 771 46 Olomouc, Czech Republic., Soural M; Department of Organic Chemistry, Faculty of Science, Palacký University, 771 46 Olomouc, Czech Republic.; Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 5, 779 00 Olomouc, Czech Republic. |
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| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2022 Apr 15; Vol. 87 (8), pp. 5242-5256. Date of Electronic Publication: 2022 Mar 28. |
| DOI: | 10.1021/acs.joc.2c00039 |
| Abstrakt: | Herein, we report a multistep synthesis of polycyclic tetrahydroisoquinolines and tetrahydrobenzo[ d ]azepines starting from Wang resin-immobilized allylglycine. After sulfonylation with 2/4-nitrobenzenesulfonyl chlorides, Mitsunobu alkylation with various phenylalkynols yielded the corresponding (phenylprop-2-yn-1-yl)-sulfonamides. "Interior" ring-closure enyne metathesis (RCEM) using a Grubbs catalyst second generation (Ru2) yielded functionalized tetrahydroisoquinoline/tetrahydrobenzo[ d ]azepine intermediates. "East-side" [4 + 2] cycloaddition with representative dienophiles was followed by the "west-side" construction of different heterocycles using various electrophiles to finally furnish a set of novel molecular frameworks bearing fused [6 + 6] or [6 + 7] rings. The developed methodology enables the facile parallel synthesis of novel, pharmacologically promising compounds derived from privileged scaffolds. |
| Databáze: | MEDLINE |
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