NaNO₂-catalyzed reaction of cyclohexenone-MBH acetates: A convenient synthesis of 2-methylene-3-cyclohexenones

A Synthesis of α-Alkyl Cycloenones by Pd-Catalyzed Suzuki–Miyaura Coupling with Cyclic Morita–Baylis–Hillman Adducts

“…The crude product was purified by flash column chromatography (petroleum ether/ethyl acetate = 20/1) as yellow solid (34.0 mg, 76%). The NMR data were in accordance with the literature report. 1 H NMR (500 MHz, CDCl 3 ) δ 8.25–8.04 (m, 2H), 7.41–7.36 (m, 2H), 7.19–7.12 (m, 2H), 6.93–6.88 (m, 1H), 6.77 (dd, J = 8.0, 1.1 Hz, 1H), 4.91 (s, 1H), 4.08 (s, 2H). 13 C­{1H} NMR (126 MHz, CDCl 3 ) δ 153.4, 148.6, 146.4, 131.0, 129.5, 128.3, 125.7, 123.6, 121.2, 115.5, 36.0.…”

Synthesis of 2-benzyl N-substituted anilines via imine condensation–isoaromatization of (E)-2-arylidene-3-cyclohexenones and primary amines

“…To date, although plentiful amination–aromatization approaches for the preparation of anilines have been well-established, to develop novel and efficient synthetic methods still remains highly desirable. In continuation of our recent studies on synthetic applications of Morita–Baylis–Hillman (MBH) adducts [ 20 – 21 ], we were interested in further utilizing ( E )-2-arylidene-3-cyclohexenones that can be facilely synthesized from MBH alcohols to build functionalized molecules. Herein, we wish to report our preliminary study on a catalyst- and additive-free synthesis of 2-benzyl- N -substituted anilines.…”