l-Proline-Catalyzed Three-Component Reaction of 4-Chloro-3-formylcoumarin, Sodium Sulfide, and α-Halo Ketones: A Direct Approach to Thieno[3,2- c ]coumarins
| Author | Thotathil, Vandana |
| Author | Al-Zoubi, Raed M. |
| Author | Sawali, Mona |
| Author | Su, Haw Lih |
| Author | Shkoor, Mohanad |
| Available date | 2024-01-22T05:29:56Z |
| Publication Date | 2023-03-01 |
| Publication Name | Synlett |
| Identifier | http://dx.doi.org/10.1055/a-1988-1916 |
| Citation | Thotathil, V., Al-Zoubi, R. M., Sawali, M., Su, H. L., & Shkoor, M. (2023). l-Proline-Catalyzed Three-Component Reaction of 4-Chloro-3-formylcoumarin, Sodium Sulfide, and α-Halo Ketones: A Direct Approach to Thieno [3, 2-c] coumarins. Synlett, 34(04), 337-342. |
| ISSN | 09365214 |
| Abstract | A new protocol for the synthesis of thieno[3,2-c]coumarins is disclosed. In this method, a 3-formyl-2-oxo-2H-chromene-4-thiolate anion is generated in situ by treatment of 4-chloro-3-formylcoumarin with sodium sulfide. This chromene-4-thiolate undergoes an L-prolinecatalyzed substitution/Knoevenagel cascade with various α-halo ketones to afford the desired thienocoumarins in moderate to good isolated yields. This protocol eliminates the need for stoichiometric amounts of inorganic bases and the use of foul-smelling thiols. The reaction conditions tolerate a variety of α-halo ketones. |
| Sponsor | This work was supported by a Qatar University Student Grant [QUST2-CAS-2020-8] and the Medical Research Center (MRC)/Academic Health System (AHS) (Grant No. MRC-01-22-414) |
| Language | en |
| Publisher | Georg Thieme Verlag KG |
| Subject | cascade reaction multicomponent reaction organocatalysis proline catalysis thienocoumarins thiophene |
| Type | Article |
| Pagination | 337-342 |
| Issue Number | 4 |
| Volume Number | 34 |
| ESSN | 1437-2096 |
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