3295-60-1

Usage

InChI:InChI=1/C14H11NO/c1-16-12-6-7-14-11(9-12)8-10-4-2-3-5-13(10)15-14/h2-9H,1H3

Upstream product

• 26706-96-7 7-methoxy-1,2,3,4-tetrahydroacridine 
• 49742-70-3 2-methoxy-9,10-dihydroacridine 
• 16492-13-0 9-chloro-2-methoxyacridine 
• 86-38-4 6,9-dichloro-2-methoxyacridine 
• 108694-49-1 4'-methoxydiphenylamine-2-carboxaldehyde 
• 118-91-2 ortho-chlorobenzoic acid 
• 42501-87-1 1-(2-fluorophenyl)-N-(4-methoxyphenyl)methanimine 
• 1512859-13-0 C₂₁H₂₀N₂O₂ 
• 104-94-9 4-methoxy-aniline 
• 6630-33-7 ortho-bromobenzaldehyde 
• 696-62-8 para-iodoanisole 
• 529-23-7 o-aminobenzaldehyde 
• 1330681-27-0 (4-methoxyphenyl)(mesityl)iodonium trifluoromethanesulfonate 
• 271-58-9 anthranil 

Downstream Products

• 22817-17-0 acridin-2-ol 
• 77282-37-2 bromo-3 methoxy-2 acridinedione-1,4 

Relevant academic research and scientific papers

2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities

By starting from a common substrate, 2-aminobenzaldehyde, both acridines and acridones were prepared. The former were generated in high yields by copper-catalyzed N-arylation followed by acid-mediated cyclization while the latter were obtained by double copper-catalyzed N-arylation followed by cyclization under the same reaction conditions. Moreover, acridine was subjected to deprotometalation by recourse to a lithium-zinc base and converted to the corresponding 4-iodo derivative, which was involved in copper-catalyzed couplings with pyrrolidinone and pyrazole. Finally, addition of pyrazole, indole and carbazole onto the 9 position of bare acridine was improved. While moderate biological activity was noticed in melanoma cells growth inhibition, the newly prepared compounds feature interesting photophysical properties which were evaluated in a preliminary study.

Cu-catalyzed cascade reaction of isoxazoles with diaryliodonium salts for the synthesis of acridines

A straightforward and efficient synthesis of acridine derivatives via a copper-catalyzed cascade reaction among isoxazoles and diaryliodonium salts is achieved. Various mono-, multi-substituted and 9-substituted acridine derivatives could be obtained in moderate to good yields. The process has gone through tandem double arylation and Friedel-Crafts reactions.

Amine compound for inhibiting SSASASASASASASAO/VAP-1 and application thereof in medicine (by machine translation)

The invention relates to an amine compound serving as an amino urea-sensitive amine oxidase (SSASAO) and/or a vascular adhesion protein -1 (VAP AP AP-1) inhibitor and application thereof in medicine, and further relates to a pharmaceutical composition containing the compound. The compounds or pharmaceutical compositions described herein may be used to treat inflammation and/or inflammation related diseases, diabetes and/or diabetes-related diseases, psychiatric disorders, ischemic diseases, vascular diseases, fibrosis or tissue transplant rejection. (by machine translation)

Preparation method of multi-functional group acridine compound and derivative thereof

The present invention relates to a preparation method of a multi-functional group acridine compound and a derivative thereof. According to the present invention, specifically a bisphosphine ligand and palladium complex catalyzed series connection coupling/cyclization reaction is used to prepare the acridine compound represented by a formula I, wherein various groups are defined in the specification; and the method has advantages of mild reaction condition, simple operation and wide substrate applicability, and the multi-functional group acridine compound and the derivative thereof can be prepared in the high yield manner. The formula I is defined in the specification.

Facile synthesis of acridines via Pd(0)-diphosphine complex-catalyzed tandem coupling/cyclization protocol

A facile and efficient approach for the synthesis of a variety of acridines via the tandem coupling/cyclization of substituted 2-bromobenzaldehydes and anilines is described. The reaction can be accomplished with ease in the presence of a catalytic amount of Pd2(dba)3 and diphosphine ligand dppf, providing a broad range of substituted acridines in good to excellent yields (up to 99%). The Lewis acid, AlCl3, is required to promote the cyclization for less electron-rich anilines.

Facile synthesis of acridine derivatives by ZnCl2-promoted intramolecular cyclization of o -arylaminophenyl schiff bases

A concise and efficient method for the synthesis of a wide range of acridine derivatives and polycyclic aza-aromatic compounds from a ZnCl 2-promoted cyclization reaction of readily available o-arylaminophenyl Schiff base compounds under convenient conditions was developed. Reaction conditions and scope of the new method were examined in detail.

Bridgehead nitrogen heterocycles which contain the quinazoline moiety - Synthesis and cycloaddition of 1,2-dihydroquinazoline 3-oxides

A novel synthesis of 1,2-disubstituted 1,2-dihydroquinazoline 3-oxides 8 and the first ever examples of 1,3-dipolar trapping of these nitrones to homonuclear dipolarophiles is described. The new dipoles 8 reacted with N-methyl maleimide, generating diastereomeric adducts 14-16. In the reaction between 8 and dimethyl acetylenedicarboxylate, primary cycloadducts 17 and/or stable rearrangement products, azomethine ylides 18, are formed depending on the substitution pattern of the dipole. The structure of 18c is unambiguously assigned by X-ray crystallographic analysis. An X-ray crystal structure determination is also presented for the cyclopropylisoxazoloquinazoline 22 formed by a [3 + 2] addition of 8a to 21, the dimethyl acetylenedicarboxylate tetramer. The Royal Society of Chemistry 2005.

N-arylation of isatins

A process for the N-arylation of isatins with organo bismuth reagents is disclosed.

Nickel-Catalyzed Transformations of 2,1-Benzisoxazoles with Organozinc Reagents

A novel transformation of 2,1-benzisoxazoles (anthranils) involving nitrogen-oxygen bond rupture with concomitant nitrogen-carbon bond formation by reaction with aryl-, methyl, or 2-thienylzinc chlorides in the presence of nickel catalyst is described.The products of the reaction are o-(substituted-amino)benzaldehydes and benzophenones, precursors of a series of heterocyclic derivatives, including acridines, quinolones, and the novel 7-chloro-1,3-dihydro-1,5-diphenyl-2H-1,4-benzodiazepin-2-one (21)

Hydride transfer reaction. A kinetic study of oxidation of 2- and 3-methoxy-N-methylacridans by some ? acceptors and a one-electron oxidant

Relative rates of oxidation of N-methylacridan (1a), 2-methoxy-N-methylacridan (1b), and 3-methoxy-N-methylacridan (1c) have been investigated as a probe of transition state structure in hydride transfer reactions.Oxidants investigated cover a 2E7-fold (with 1a) to 2E8-fold (with 1c) range of reactivity, and include the ? acceptors 1,4-benzoquinone (BQ), p-chloranil (CA), 2,3-dicyano-1,4-benzoquinone (DCBQ), 7,7,8,8-tetracyanoquinodimethane (TCNQ), and tetracyanoethylene (TCNE) in acetonitrile (AN), BQ in 50:50 (v/v) AN-water, and the one -electron oxidant tris(2,2'-bipyridyl)cobalt(III), Co(bipy)33+, in AN, all at 25 deg C.For all of ? acceptors except TCNE the order of reactivity, 1c > 1b > 1a, (DH) indicates a transition state resembling the corresponding acridium ion product (D+), while the order of reactivity with Co(bipy)33+, 1b > 1c > 1a, indicates a transition state resembling the acridan radical cation (DH+.).The order of reactivity observed with TCNE, 1b ca. 1c > 1a, is tentatively interpreted as indicating a transition state resembling the corresponding 9-acridanyl radical (D.).