10409-20-8Relevant academic research and scientific papers
Pd(II)-Catalyzed Synthesis of Alkylidene Phthalides via a Decarbonylative Annulation Reaction
Borthakur, Somadrita,Baruah, Swagata,Sarma, Bipul,Gogoi, Sanjib
, p. 2768 - 2771 (2019/04/16)
An unprecedented Pd(II)-catalyzed decarbonylative C-H/C-C activation and annulation reaction, which proceeds via intramolecular cyclization, is reported. This reaction of hydroxynaphthoquinones with disubstituted alkynes provides good yields of substituted alkylidene phthalides, which are the key intermediates for the synthesis of bioactive natural products.
Styryl and functionalized aryl derivatives of lawsone through metal-free cross-coupling of its BF3-activated phenyliodonium ylide with cinnamaldehydes and arylaldehydes
Malamidou-Xenikaki, Elizabeth,Tsanakopoulou, Maria,Chatzistefanou, Maria,Hadjipavlou-Litina, Dimitra
, p. 5650 - 5661 (2015/08/03)
Phenyliodonium ylide of lawsone activated with BF3?Et2O reacts with cinnamaldehydes to afford 2-hydroxy-3-styryl-1,4-naphthoquinones in good to excellent yields and relatively high level of stereospecificity through deformylation of the aldehydes. The product yield is diminished with a methoxy substituted cinnamaldehyde and becomes zero with a dimethoxy substituted substrate giving rise to another product, 2-hydroxy-3-aryl-1,4-naphthoquinone. The reaction of the same ylide with salicylic aldehydes forms 2-hydroxy-3-(2-hydroxyaryl)-1,4-naphthoquinones and/or benzo[d]naphtha[2,1-b]furano-5,6-diones, depending on the reaction conditions applied. Plausible reaction mechanisms explaining the formation of these products are proposed. The products showed potent antioxidant activity and inhibited lipoxygenase.
Arylation of lawsone through BF3-mediated coupling of its phenyliodonium ylide with activated arenes and aromatic aldehydes
Glinis, Elias,Malamidou-Xenikaki, Elizabeth,Skouros, Haris,Spyroudis, Spyros,Tsanakopoulou, Maria
experimental part, p. 5786 - 5792 (2010/09/09)
Phenyliodonium ylide of lawsone, activated by BF3·Et 2O, reacts with electron-rich arenes to afford the corresponding 2-aryl-3-hydroxy-1,4-naphthoquinones, in a coupling reaction without metal catalysts. The same type of products, in greater variety and higher yields, are obtained from the reaction of the BF3·Et2O- activated ylide with aromatic aldehydes in a synthetically and mechanistically interesting deformylation reaction.
