95216-56-1

Upstream product

• 52548-14-8 2-iodoyl-5-methylbenzoic acid 
• 62-53-3 aniline 
• 6967-82-4 2-bromo-5-methylbenzoic acid 
• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 108-86-1 bromobenzene 

Downstream Products

• 95216-65-2 5-methyl-2-anilinobenzamide 
• 70344-62-6 2-Isopropyl-6-methyl-1-phenyl-1H-quinazolin-4-one 
• 1428865-10-4 methyl 5-methyl-2-(methyl(phenyl)amino)benzoate 
• 1428865-35-3 5-methyl-2-(methyl(phenyl)amino)benzaldehyde 
• 1428865-23-9 C₁₅H₁₇NO 

Relevant academic research and scientific papers

Syntheses and evaluation of new acridone derivatives for selective binding of oncogene c-: Myc promoter i-motifs in gene transcriptional regulation

We synthesized a series of acridone derivatives for specific binding ligands of i-motifs. Subsequent evaluations showed that B19 could selectively bind to and stabilize the c-myc promoter i-motif without significant binding to the G-quadruplex and duplex

Acid-catalyzed oxidative cross-coupling of acridans with silyl diazoenolates and a Rh-catalyzed rearrangement: two-step synthesis of γ-(9-acridanylidene)-β-keto esters

A MsOH-catalyzed oxidative cross-coupling of acridans and silyl diazoenolates and a Rh2(OAc)4-catalyzed rearrangement of the resultant diazo products are described. The reactions provide various γ-(9-acridanylidene)-β-keto esters in good yields, which bear an active α-methylene unit for further functionalization.

Light-Driven Intramolecular C?N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex

Reported herein is a visible-light-driven intramolecular C?N cross-coupling reaction under mild reaction conditions (metal- and photocatalyst-free, at room temperature) via a long-lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N-substituted polycyclic quinazolinone derivatives with a broad substrate scope (>50 examples) and further exploited to synthesize the natural products tryptanthrin, rutaecarpine, and their analogues. The success of gram-scale synthesis and solar-driven transformation, as well as promising tumor-suppressing biological activity, proves the potential of this strategy for practical applications. Mechanistic investigations, including control experiments, DFT calculations, UV-vis spectroscopy, EPR, and X-ray single-crystal structure of the key intermediate, provides insight into the mechanism.

ELECTROCHROMIC COMPOUND, ELECTROCHROMIC COMPOSITION, AND ELECTROCHROMIC ELEMENT

PROBLEM TO BE SOLVED: To provide an electrochromic compound which enables stable operation and provides good yellow color development. SOLUTION: The electrochromic compound is represented by the following formula. Preferably, at least one of R5 and R15 is a polymerizable functional group. (R1 to R8 and R11 to R18 are each independently H, a halogen atom, a monovalent organic group, or a polymerizable functional group, provided that the monovalent organic group and the polymerizable functional group may be further substituted with a substituent; and R9, R10, R19 and R20 are each independently H, an alkyl group, or an aryl group.) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

NIS-mediated intramolecular oxidative α-functionalization of tertiary amines: Transition metal-free synthesis of 1,2-dihydro-(4H)-3,1-benzoxazin-4-one derivatives

A novel method for direct α-functionalization of tertiary amines via NIS-mediated oxidative C-O bond formation, where NIS serves as both an oxidant and an iodination reagent, has been developed. The method provides easy access to either iodinated or non-iodinated 1,2-dihydro-(4H)-3,1-benzoxazin-4-ones, depending on the nature of the reactant, via a regioselective transition metal-free approach. This journal is

PhI(OAc)2-mediated intramolecular oxidative aryl-aldehyde C sp 2-C sp 2 bond formation: Metal-free synthesis of acridone derivatives

A metal-free protocol for direct aryl-aldehyde Csp2-Csp 2 bond formation via a PhI(OAc)2-mediated intramolecular cross-dehydrogenative coupling (CDC) of various 2-(N-arylamino)aldehydes was developed. The novel methodology requires no need of preactivation of the aldehyde group, is applicable to a large variety of functionalized substrates, and most of all provides a convenient approach to the construction of biologically important acridone derivatives.

Sc(OTf)3-catalyzed dehydrogenative cyclization for synthesis of N-methylacridones

A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)3 and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.

Preparation and characterization of thermochemiluminescent acridine-containing 1,2-dioxetanes as promising ultrasensitive labels in bioanalysis

Thermochemiluminescence is the luminescence process in which a thermodynamically unstable molecule decomposes with light emission when heated above a threshold temperature. We recently reported the thermochemiluminescence properties of an acridine-containing 1,2-dioxetane, which emits at relatively low temperatures (i.e., below 100 C). Herein, we explored the effect of the introduction of methyl substituents in the acridine system. The methyl group did not determine an excessive destabilization of 1,2-dioxetane ring nor significantly affect the general physical properties of the molecule. Monosubstituted methyl derivatives and a series of derivatives bearing several combinations of two, three, and four methyl groups were prepared. The rate of formation of 1,2-dioxetane derivatives 1b-k strongly depended on the methyl substitution pattern. All members of this library of mono-, di-, tri-, and tetramethyl-substituted derivatives were characterized in terms of photophysical and thermochemiluminescence properties. The introduction of methyl groups into the acridine ring caused a marked decrease in the activation energy of the thermochemiluminescent reaction. Tri- and tetramethyl-substituted acridones had the highest fluorescence quantum yields, in the range 0.48-0.52, and the corresponding 1,2-dioxetanes 1h and 1j showed in thermochemiluminescence imaging experiments limit of detection values more than ten times lower with respect to the unsubstituted derivative.

Studies on 4(1H)-quinazolinones. 5. Synthesis and antiinflammatory activity of 4(1H)-quinazolinone derivatives

A number of new 4(1H)-quinazolinones were synthesized and evaluated in the carrageenin-induced paw edema test. Most of the compounds were obtained by the cyclization of the appropriately substituted anthranilamides with acid chlorides, followed by further chemical transformation. Structure-activity data suggest that 2-isopropyl-1-phenyl-, 2-cyclopropyl-1-phenyl-, and 1-isopropyl-2-phenyl-4(1H)-quinazolinones afford optimal potency and the presence of a halogen atom is preferred for activity. Adrenalectomy does not affect the antiinflammatory test results. The best result taking into account both efficacy and side effects was displayed by 1-isoproyl-(2-fluorophenyl)-4(1H)-quinazolinone.