33738-96-4Relevant articles and documents
Access to Electron-Deficient 2,2-Disubstituted Chromanes: A Highly Regioselective One-Pot Synthesis via an Inverse-Electron-Demand [4 + 2] Cycloaddition of ortho-Quinone Methides
Tanaka, Kenta,Kishimoto, Mami,Asada, Yosuke,Tanaka, Yuta,Hoshino, Yujiro,Honda, Kiyoshi
, p. 13858 - 13870 (2019)
We report the one-pot synthesis of 2,2-disubstituted chromanes with electron-withdrawing substituents. This reaction provides a simple yet efficient route to a wide range of electron-deficient chromanes in high yield and excellent regioselectivity. The reaction of salicylaldehyde with 1,1-disubstituted ethylenes smoothly furnishes these electron-deficient chromanes, which can be further transformed into functionalized chromanes or chromene. For example, BW683C was effectively synthesized from 5-chlorosalicylaldehyde with 4-chlorostyrene in two steps in excellent yield. The present reaction thus provides versatile access to functionalized electron-deficient chromanes and chromenes and therefore constitutes a promising tool for the synthesis of biologically and photochemically active molecules.
Temperature-controlled divergent synthesis of 4-alkoxy- or 4-alkenyl-chromanes via inverse electron-demand cycloaddition with in situ generated ortho-quinone methides
Tanaka, Kenta,Kishimoto, Mami,Hoshino, Yujiro,Honda, Kiyoshi
supporting information, p. 1841 - 1845 (2018/04/11)
The temperature-controlled divergent synthesis of 4-alkoxy- or 4-alkenyl-chromanes via inverse electron-demand cycloaddition with in situ generated ortho-quinone methides under identical reaction conditions except for thermal condition has been developed. At room temperature, the reaction generated 4-methoxychromanes, whereas the reaction performed at room temperature to 100 °C gave 4-alkenylchromanes. Trifluoromethanesulfonic acid was efficiently suitable in the reaction to give the 4-substituted chromanes. This divergent synthetic strategy exhibits a new method giving carbon–carbon or carbon–oxygen bond by controlling the reaction temperature.