2033-88-7

Upstream product

• 2033-89-8 3,4-dimethoxyphenol 
• 26944-31-0 N,N-Diformylacetamide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 79-21-0 peracetic acid 
• 64-19-7 acetic acid 

Downstream Products

• 7203-46-5 3,4-dimethoxyphenyl acetate 
• 120-08-1 Scoparone 
• 1279586-99-0 3,4-dimethoxyphenyl (2E)-3-(dimethylamino)prop-2-enoate 
• 14382-91-3 2-hydroxy-4,5-dimethoxybenzaldehyde 
• 2033-89-8 3,4-dimethoxyphenol 

Relevant academic research and scientific papers

IMPROVED OXIDATION PROCEDURE WITH AROMATIC PEROXYACIDS

The application of the m-Chloroperbenzoic acid-potassium fluoride system in the Baeyer-Villinger oxidation of aromatic aldehydes and in the epoxidation of olefins has been studied.

Facile synthesis and nitric oxide inhibitory activity of aurones, rugaurone a, gramflavonoid a and their derivatives

Facile synthesis of natural aurones, rugaurone A (1a), gramflavonoid A (1b) and their novel derivatives (1c-1o) is accomplished in good to high yields with exceptional Z-selectivity (≥ 97%) from the commercially available starting materials. Herein, practically improved method was developed for the synthesis of common key intermediate, 5,6-dimethoxybenzofuran-3(2H)-one (5). Later, their nitric oxide (NO) production inhibition effects were estimated in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages as an indicator of anti-inflammatory activity. All compounds exhibited weak to good strength against NO production in a concentration-dependent manner and none of the compound showed significant cytotoxicity against macrophages at the highest (10 μM) concentration. The IC50 values are showed in the range from 3.39 to 19.55 μM. Among the 15 aurones synthesized in this study, 3 compounds that is compound 1g (63.98%) followed by compound 1o (49.07%) and rugaurone A (1a) (41.72%) showed the maximum inhibitory activity with respective IC50 values of 4.50 μM, 4.98 μM and 3.39 μM compared to L-NMMA (IC50 = 5.19 μM), which was used as a standard NO inhibitor. This study suggests that compounds 1g, 1o and 1a may serve as favorable structures for further development of NO production-targeted anti-inflammatory agents.

Acceleration of the Dakin reaction by trifluoroacetic acid

An acceleration of the Dakin reaction caused by addition of trifluoroacetic acid is described. The modified protocol converts aromatic aldehydes to the corresponding phenols within 4 hours at room temperature by means of hydrogen peroxide in acidic medium. This acceleration is attributed to the stability of hydrogen peroxide in an acidic medium. This modified protocol provides alternative and easy access to important phenolic precursors that have been used in the synthesis of various natural products.

New approach for the construction of the coumarin frame and application in the total synthesis of natural products

A new synthetic approach is described for building the coumarin scaffold through the Lewis acid-promoted cyclization of novel aryl 3-(dimethylamino)prop- 2-enoates 2a - 2f. The latter precursors were prepared via aminomethylenation of the corresponding aryl acetates 4a - 4f with the Bredereck reagent. This approach was used for the synthesis of biologically active natural compounds 1a - 1f, through a three-step procedure starting from the corresponding phenols.

Synthesis of 1,2,4-trimethoxybenzene and its selective functionalization at C-3 by directed metalation

A new and efficient strategy was developed for the preparation of 1,2,4-trimethoxybenzene (3, a powerful attractant of Euglossini bees) and its C-3 derivatives (7a-j), from vanillin (2) in 56% overall yield.

Synthesis of lamellarin U and lamellarin G trimethyl ether by alkylation of a deprotonated α-aminonitrile

(Chemical Equation Presented) 1,2,3,4-Tetrahydroisoquinoline-1- carbonitriles can serve as starting materials for the one-pot synthesis of 5,6-dihydropyrrolo[2,1a]isoquinolines and 1-benzyl-3,4-dihydroisoquinolines. The latter compounds were transformed to lamellarin G trimethyl ether and lamellarin U in short reaction sequences. This method allows the introduction of acid-sensitive protecting groups for the phenolic hydroxy functions which would be cleaved under the harsh conditions of the classical Bischler-Napieralski reaction.

Baeyer-Villiger oxidations in ionic liquids. A facile conversion of ketones to esters and lactones

A variety of cyclic and acyclic ketones underwent readily oxidation with m-chloroperbenzoic acid (m-CPBA) in ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate [bmim]BF4 to afford esters/lactones with high selectivity, ease of product separation and in excellent chemical yields. The reaction proceeded smoothly in ionic liquid without the need of any additional acid or base catalyst. The ketones show enhanced reactivity in ionic liquids thereby reducing reaction times and improving the yields significantly.

ALDEHYDE CONVERSION METHOD USING A MOLECULAR SIEVE AND THE USE OF THE MOLECULAR SIEVE AS A CATALYST IN SAID METHOD

The inversion relates to an aldehyde conversion method comprising putting an aldehyde into contact with oxygenated water and with a catalyst, under oxidation conditions, wherein the catalyst is a molecular sieve with pores of a diameter of at least 0.52 nm and has an empirical formula in a calcined and dehydrated form of(SnxTiySi1-x-y-zGez) O2 wherein x is a molar fraction of the tin and has a value between 0.001 and 0.1; y is a molar fraction of titanium and has a value from zero to 0.1; and z is the molar fraction molar of the germanium and has a value from zero to 0.08.

Orthoamides, LVI [1]. A new method of wide scope for the preparation of aryl formates

Aryl formates 4a-u, 6, 8, 10, 12, 14, 16, 18, 20, 22, 24, 26 are prepared by formylation of hydroxyarenes 3a-u, 5, 7, 9, 11, 13, 15, 17, 19, 21, 23, 25 with N,N-diformylacetamide (1) or triformamide (2), respectively, in fairly good yields. The reactions can be catalyzed by sodium diformamide or praseodymium(III) triflate. The thiolformate 28 was obtained analogously from 1-thionaphthol (27).

The oxidation of methoxy aromatic aldehydes with the system O2/iPrCHO/metal catalyst

The oxidation of methoxy aromatic aldehydes by the system O2/iPrCHO/metal catalyst proceeds in high yields of formates, almost without the formation of important quantities of carboxylic acids.