| Autor: |
Reddy RJ; Department of Chemistry, University College of Science, Osmania University, Hyderabad 500 007, India., Kumari AH; Department of Chemistry, University College of Science, Osmania University, Hyderabad 500 007, India., Krishna GR; Centre for X-ray Crystallography, CSIR-National Chemical Laboratory, Pune 411 008, India. |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2023 Feb 03; Vol. 88 (3), pp. 1635-1648. Date of Electronic Publication: 2023 Jan 17. |
| DOI: |
10.1021/acs.joc.2c02696 |
| Abstrakt: |
Benzoheteroles are valuable scaffolds in medicinal chemistry, but the direct synthesis of 3-vinyl benzoheterole analogues remains unexplored. A rationally designed new class of 1,6-enyne-containing propargylic alcohols has been prepared for the modular synthesis of 3-alkenyl benzoheteroles. Ag-catalyzed cascade radical sulfonylative-cycloannulation of 1,6-enynols with sodium sulfinates is realized to access a wide variety of 2,3-disubstituted benzoheteroles in good to high yields. Moreover, a three-component coupling of 1,6-enynols, aryldiazonium salts, and Na 2 S 2 O 5 (as an SO 2 surrogate) has been achieved to deliver benzoheterole derivatives in moderate to good yields. Of note, a scalable reaction and late-stage synthetic transformations were successfully demonstrated. A plausible mechanism is also presented based on the existing experimental results and control experiments. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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