Base-Promoted Chemodivergent Construction of 2 H -Chromen-2-one and Chromeno[2,3- c ]pyrrole Scaffolds from para -Quinone Methides and α-Alkylidene Succinimides.
| Autor: | Roshani K; Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand 247667, India., Raza MS; Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand 247667, India., Peddinti RK; Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand 247667, India. |
|---|---|
| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2024 Oct 25; Vol. 26 (42), pp. 9114-9119. Date of Electronic Publication: 2024 Oct 11. |
| DOI: | 10.1021/acs.orglett.4c03436 |
| Abstrakt: | Herein, we evolve a base-promoted synthesis of 2 H -chromen-2-one and chromeno[2,3- c ]pyrrole scaffolds via (4 + 2) annulation of α-alkylidene succinimides with 2-hydroxyphenyl-substituted para -quinone methides ( p -QMs). Extremely selective and switchable cyclizations were obtained by modifying the base. This metal-free protocol is highlighted by its mild reaction conditions and broad substrate scope, and the viability of the existing protocol was additionally illustrated by gram-scale synthesis and further modification. Several control experiments were performed to understand the reaction mechanism. |
| Databáze: | MEDLINE |
| Externí odkaz: |
|