jo6b01242_si_001.pdf (17.51 MB)

A Palladium-Catalyzed Method for the Synthesis of 2‑(α-Styryl)-2,3-dihydroquinazolin-4-ones and 3‑(α-Styryl)-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide: Access to 2‑(α-Styryl)quinazolin-4(3H)‑ones and 3‑(α-Styryl)-1,2,4-benzothiadiazine-1,1-dioxides

Download (17.51 MB)
journal contribution
posted on 25.07.2016 by Priyanka Kundu, Amrita Mondal, Chinmay Chowdhury
An efficient synthesis of 2-(α-styryl)-2,3-dihydro­quinazolin-4-ones and 3-(α-styryl)-3,4-dihydro-1,2,4-benzo­thiadiazine-1,1-dioxides has been achieved in 39–94% yield through palladium-catalyzed cyclocondensation of aryl/vinyl iodides with allenamides 1315 and 22, respectively. Base treatment of the N-tosylated products provides an easy access to 2-(α-styryl)­quinazolin-4­(3H)-ones and 3-(α-styryl)-1,2,4-benzo­thiadiazine-1,1-dioxides, hitherto unknown heterocycles. The method has been tested with phenyl substituted allenamides, applied for bis-heteroannulation, and used in the preparation of analogues of the natural product Luotonin F.