135-45-5

Usage

Uses

Used in Pharmaceutical Industry:
N-(2,5-DIMETHOXYPHENYL) BENZAMIDE is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique chemical structure allows it to interact with biological targets, potentially leading to the development of new therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, N-(2,5-DIMETHOXYPHENYL) BENZAMIDE is used as a precursor in the production of pesticides and other agrochemicals. Its chemical properties may contribute to the effectiveness of these products in controlling pests and diseases in agriculture.
Used in Material Sciences:
N-(2,5-DIMETHOXYPHENYL) BENZAMIDE also finds applications in material sciences, where it can be used to develop new materials with specific properties. Its amide and dimethoxyphenyl groups may influence the material's characteristics, such as solubility, stability, and reactivity, making it suitable for various applications in this field.

Upstream product

• 98-88-4 benzoyl chloride 
• 102-56-7 2,5-dimethoxyaniline 
• 221541-73-7 N-(2,5-dimethoxyphenyl)thiobenzamide 
• 2100-42-7 2-chloro-1,4-dimethoxybenzene 
• 55-21-0 benzamide 
• 591-50-4 iodobenzene 
• 3467-59-2 2,5-dimethoxyacetanilide 
• 199620-14-9 chromium⁽⁰⁾ hexacarbonyl 

Downstream Products

• 92-20-6 N-(2,5-Dimethoxy-4-nitrophenyl)benzamide 
• 221541-73-7 N-(2,5-dimethoxyphenyl)thiobenzamide 
• 221541-72-6 N-(4-Bromo-2,5-dimethoxyphenyl)benzamide 
• 221541-80-6 4,7-Dioxo-2-phenylbenzothiazole 
• 221541-76-0 4,7-dimethoxy-2-phenyl-1,3-benzothiazole 
• 221541-83-9 6-Bromo-4,7-dioxo-2-phenylbenzothiazole 
• 221541-74-8 N-(4-bromo-2,5-dimethoxyphenyl)thiobenzamide 
• 221541-78-2 N-(6-Bromo-4,7-dimethoxy-2-phenyl)benzothiazole 
• 60890-09-7 2-benzamido-1,4-benzoquinone 
• 1616268-53-1 4-([1,4'-bipiperidin]-1'-ylmethyl)-2-phenylbenzo[d]oxazol-5-ol 
• 116496-29-8 5-hydroxy-2-phenylbenzoxazole 

Relevant academic research and scientific papers

Unique ring expansion of a 6-3 bicyclic ring system forming a functionalized 7-membered ring accelerated by nitrogen functional groups

The treatment of (2-hydroxy-5-oxobicyclo [4.1.0] hept-3-en-3-yl) carbamic acid esters and (2-hydroxy-5-oxobicyclo [4.1.0] hept-3-en-3-yl) benzamide with TMSCl gave 7-membered ring compounds in good yields. The structure of the substituent at the C3 position of the cyclohexene ring is crucial for this ring expansion. The reaction mechanism is thought to involve the formation of a norcaradiene (bicyclo [4.1.0] hept-2,4-diene) structure and subsequent electrocyclic reaction.

The use of Cr (CO)6 as an alternative CO source in Pd-catalyzed C-N bond formation: Synthesis of benzamides

An efficient strategy for the synthesis of benzamides from acetamides and aryl iodides using 1?mol% Pd (OAc)2 as catalyst and Cr (CO)6 as CO-precursor is described. This new synthetic methodology displays high functional group tolerance on both substrates and avoids the need for ligands, reducing agents, or other additives. The corresponding products were obtained in good to excellent yields at atmospheric pressure under mild reaction conditions.

Natural Abenquines and Their Synthetic Analogues Exert Algicidal Activity against Bloom-Forming Cyanobacteria

Abenquines are natural quinones, produced by some Streptomycetes, showing the ability to inhibit cyanobacterial growth in the 1 to 100 μM range. To further elucidate their biological significance, the synthesis of several analogues (4f-h, 5a-h) allowed us to identify some steric and electronic requirements for bioactivity. Replacing the acetyl by a benzoyl group in the quinone core and also changing the amino acid moiety with ethylpyrimidinyl or ethylpyrrolidinyl groups resulted in analogues 25-fold more potent than the natural abenquines. The two most effective analogues inhibited the proliferation of five cyanobacterial strains tested, with IC50 values ranging from 0.3 to 3 μM. These compounds may be useful leads for the development of an effective strategy for the control of cyanobacterial blooms.

Natural abenquines and synthetic analogues: Preliminary exploration of their cytotoxic activity

In this study, we explore the cytotoxic activity of four natural abenquines (2a–d) and fourteen synthetic analogues (2e–j and 3a–h) against a panel of six human cancer cell lines using a SRB assay. It was found that most of the compounds revealed higher levels of cytotoxic activities than naturally occurring abenquines. The analogues carrying ethylpyrrolidinyl and ethylpyrimidinyl with either an acetyl group (2?h–i) or a benzoyl group (3f–g), were the most potent against all human cancer cell lines and displayed EC50 between a range of 0.6–3.4?μM. Notably, of the compounds tested, compound 2i proved the most cytotoxic against both ovarian (A2780) and breast (MCF7) cells, showing EC50?=?0.6 and 0.8?μM respectively. Likewise, the analogues 2i, 3f and 3?g showed strong activity against cell HT29 with EC50?=?0.9?μM for these compounds.

Generating Active L-Pd(0) via Neutral or Cationic π-Allylpalladium Complexes Featuring Biaryl/Bipyrazolylphosphines: Synthetic, Mechanistic, and Structure-Activity Studies in Challenging Cross-Coupling Reactions

Two new classes of highly active yet air- and moisture-stable π-R-allylpalladium complexes containing bulky biaryl- and bipyrazolylphosphines with extremely broad ligand scope have been developed. Neutral π-allylpalladium complexes incorporated a range of biaryl/bipyrazolylphosphine ligands, while extremely bulky ligands were accommodated by a cationic scaffold. These complexes are easily activated under mild conditions and are efficient for a wide array of challenging C-C and C-X (X = heteroatom) cross-coupling reactions. Their high activity is correlated to their facile activation to a 12-electron-based L-Pd(0) catalyst under commonly employed conditions for cross-coupling reactions, noninhibitory byproduct release upon activation, and suppression of the off-cycle pathway to form dinuclear (μ-allyl)(μ-Cl)Pd2(L)2 species, supported by structural (single crystal X-ray) and kinetic studies. A broad scope of C-C and C-X coupling reactions with low catalyst loadings and short reaction times highlight the versatility and practicality of these catalysts in organic synthesis.

Benzofuran derivatives as anticancer inhibitors of mTOR signaling

A series of 32 derivatives and isosteres of the mTOR inhibitor 2 were synthesized and compared for their cytotoxicity in radioresistant SQ20B cancer cell line. Several of these compounds, in particular 30b, were significantly more cytotoxic than 2. Importantly, 30b was shown to block both mTORC1 and Akt signaling, suggesting insensitivity to the resistance associated to Akt overactivation observed with rapamycin derivatives currently used in clinic.

Synthesis and application of palladium precatalysts that accommodate extremely bulky Di-tert-butylphosphino biaryl ligands

A series of palladacyclic precatalysts that incorporate electron-rich di-tert-butylphosphino biaryl ligands is reported. These precatalysts are easily prepared, and their use provides a general means of employing bulky ligands in palladium-catalyzed cross-coupling reactions. The application of these palladium sources to various C-N and C-O bond-forming processes is also described.

Phosphine-Ligated Palladium Sulfonate Palladacycles

Described are palladium precatalysts, and methods of making and using them. The palladium precatalysts show improved stability and improved reactivity in comparison to previously-described palladium precatalysts.

Thermally induced cyclization of electron-rich N-arylthiobenzamides to benzothiazoles

Heating N-(2-methoxyphenyl)benzenecarbothioamides in refluxing nitrobenzene for 24 hours gives the corresponding benzothiazoles with intramolecular ipso substitution of the ortho-methoxy substituent. The thermal cyclization of various other N-arylthiobenzamides is also explored. Georg Thieme Verlag Stuttgart · New York.