5293-52-7

Upstream product

• 917-64-6 methyl magnesium iodide 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 54370-00-2 2-bromo-4,5-dimethoxybenzyl alcohol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 676-58-4 methylmagnesium chloride 
• 74-83-9 methyl bromide 
• 75-16-1 methylmagnesium bromide 
• 74-88-4 methyl iodide 

Downstream Products

• 151694-58-5 2-methyl-2-(2-bromo-4,5-dimethoxyphenyl)-1,3-oxathiolane 
• 157749-07-0 2'-(2-methyl-1,3-oxathiolan-2-yl)-4,4',5,5'-tetramethoxybiphenyl-2-carboxaldehyde 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 1354364-37-6 2-(2-bromo-4,5-dimethoxyphenyl)butan-2-ol 
• 1401416-10-1 ethyl (2E)-3-{2-[1-(3-ethoxy-3-oxopropoxy)ethyl]-4,5-dimethoxyphenyl}acrylate 
• 1401416-26-9 tert-butyl (2E)-3-{2-[1-(3-tert-butoxy-3-oxopropoxy)ethyl]-4,5-dimethoxyphenyl}acrylate 
• 1398756-71-2 C₁₅H₂₁BrO₃ 
• 321681-28-1 2-bromo-1-(2-bromo-4,5-dimethoxyphenyl)-ethanone 
• 1233979-74-2 (Z)-N'-[1-(2-bromo-4,5-dimethoxyphenyl)ethylidene]-4-methylbenzenesulfonohydrazide 
• 1233979-79-7 5,6-dimethoxy-3-methyl-1-(p-tolylsulfonyl)indazole 
• 1616667-69-6 ethyl (2E)-3-(2-bromo-4,5-dimethoxyphenyl)but-2-enoate 

Relevant academic research and scientific papers

α-Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles

A novel palladium-catalyzed decarboxylative cascade cyclization for the assembly of diverse fused heteropolycycles by employing α-oxocarboxylic acids as three-carbon insertion units is reported. This protocol enables the synthesis of isoquinolinedione- and indolo[2,1-a]isoquinolinone-fused benzocycloheptanones in moderate to good yields by the use of different aryl iodides, including alkene-tethered 2-iodobenzamides and 2-(2-iodophenyl)-1H-indoles. Notably, the approach achieves simultaneous construction of both six- and seven-membered rings via sequential intramolecular carbopalladation, C-H activation, and decarboxylation.

Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids

A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O2 system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.

Asymmetric Synthesis and Application of Chiral Spirosilabiindanes

Reported here is the development of a class of chiral spirosilabiindane scaffolds by Rh-catalyzed asymmetric double hydrosilation, for the first time. Enantiopure SPSiOL (spirosilabiindane diol), a new type of chiral building block for the preparation of various chiral ligands and catalysts, was readily prepared on greater than 10 gram scale using this protocol. The potential of this new spirosilabiindane scaffold in asymmetric catalysis was preliminarily demonstrated by development of the corresponding monodentate phosphoramidite ligands (SPSiPhos), which were used in both a Rh-catalyzed hydrogenation and a Pd-catalyzed intramolecular carboamination.

Asymmetric Synthesis of 1,2-Dihydronaphthalene-1-ols via Copper-Catalyzed Intramolecular Reductive Cyclization

We describe a copper-catalyzed intramolecular reductive cyclization of easily accessible benz-tethered 1,3-dienes containing a ketone moiety. This process provided biologically active 1,2-dihydronaphthalene-1-ol derivatives in good yields with excellent enantio- and diastereoselectivity. Mechanistic investigations using density functional theory revealed that (Z)- and (E)-allylcopper intermediates formed in situ from the diene and copper catalyst undergo isomerization and selective intramolecular allylation of the (E)-allylcopper form of the major product through a six-membered boatlike transition state. The resulting products were further transformed to fully saturated naphthalene-1-ols by reactions of the olefin moiety.

Phosphine- and water-promoted pentannulative aldol reaction

Herein, an efficient metal-free intramolecular aldol reaction for the synthesis of an unusual class of cyclopentanoids is described. The reaction of α-substituted dienones tethered with ketones in the presence of tributylphosphine and water provided aldols. The role of water was realised to be crucial for this transformation. Furthermore, isotopic labeling experiments provided vital information about the reaction mechanism.

From catechol-tocopherol to catechol-hydroquinone polyphenolic antioxidant hybrids

Multidefence antioxidants represent a valuable solution for the protection against oxidative stress. From the planned synthesis of a catechol-tocopherol hybrid, we isolated a catechol-hydroquinone hybrid through a BBr3-mediated benzochromene-fluoren-1-ol transposition. The compound prepared showed a remarkable chain-breaking antioxidant in the catechol portion, while the very sensitive hydroquinone moiety revealed to be an efficient generator of hydroperoxyl radicals.

PdII-Catalyzed Oxidative Tandem aza-Wacker/Heck Cyclization for the Construction of Fused 5,6-Bicyclic N,O-Heterocycles

A PdII-catalyzed oxidative tandem cyclization was developed for the construction of fused 5,6-bicyclic N, O-heterocycles. This reaction was enabled by the combined use of a 3-methylpyridine ligand and pentafluorobenzoic acid additive. A range of heterocyclic products with different substituents could be prepared in moderate to good yields via this methodology. Several transformations, including a scaled-up preparation of product 2 a, were also carried out showing the good applicability of our methodology.

Synthesis of analogues of natural antimitotic glaziovianin A based on dill and parsley seed essential oils

Glaziovianin A and its analogues were synthesized in six steps starting from allylpolyalkoxybenzenes separated from essential oils of dill (Anetum graviolens) and parsley (Petro-selinum sativum) seeds.

Efficient Synthesis of Glaziovianin A Isoflavone Series from Dill and Parsley Extracts and Their in Vitro/in Vivo Antimitotic Activity

A concise six-step protocol for the synthesis of isoflavone glaziovianin A (GVA) and its alkoxyphenyl derivatives 9 starting with readily available plant metabolites from dill and parsley seeds was developed. The reaction sequence involved an efficient conversion of the key intermediate epoxides 7 into the respective β-ketoaldehydes 8 followed by their Cu(I)-mediated cyclization into the target series 9. The biological activity of GVA and its derivatives was evaluated using a panel of seven human cancer cell lines and an in vivo sea urchin embryo assay. Both screening platforms confirmed the antimitotic effect of the parent GVA (9cg) and its alkoxy derivatives. Structure-activity relationship studies suggested that compounds 9cd and 9cf substituted with trimethoxy- and dillapiol-derived B-rings, respectively, were less active than the parent 9cg. Of the evaluated human cancer cell lines, the A375 melanoma cell line was the most sensitive to the tested molecules. Notably, the target compounds were not cytotoxic against human peripheral blood mononuclear cells up to 10 μM concentration. Phenotypic readouts from the sea urchin assay unequivocally suggest a direct microtubule-destabilizing effect of isoflavones 9cg, 9cd, and 9cf.

Palladium-Catalyzed Aerobic Aminooxygenation of Alkenes for Preparation of Isoindolinones

A palladium-catalyzed intramolecular isoindolinone-forming aminooxygenation of alkenes with 1 atm of oxygen as oxidant is reported. A variety of functionalized alkenes and carboxylic acids can be used, and high yields were observed. Preliminary mechanistic studies revealed that the aminooxygenation products were formed through the oxidation of a C-PdII species using a strong oxidant, peroxide, which is generated in situ from a Pd(OAc)2/bpy/O2/HOAc catalytic system.