393121-97-6

Upstream product

• 578-66-5 8-amino quinoline 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 67-56-1 methanol 
• 33757-48-1 N-quinolin-8-yl-benzamide 
• 98-88-4 benzoyl chloride 
• 579-75-9 2-Methoxybenzoic acid 
• 723259-89-0 2-iodo-N-(quinolin-8-yl)benzamide 

Downstream Products

• 1200444-78-5 C₁₉H₁₆N₂O₄ 
• 1215018-98-6 N-(6-styryl-2-methoxybenzoyl)-8-aminoquinoline 
• 1215019-01-4 N-(2-methoxy-6-(4-trifluoromethoxybenzyl)-benzoyl)-8-aminoquinoline 
• 1620466-21-8 (E)-2-cinnamyl-6-methoxy-N-(quinolin-8-yl)benzamide 
• 312503-18-7 2-hydroxy-N-(quinolin-8-yl)benzamide 
• 579-75-9 2-Methoxybenzoic acid 

Relevant academic research and scientific papers

Copper-mediated synthesis of quinazolin-4(3: H)-ones from N-(quinolin-8-yl)benzamide and amidine hydrochlorides

An efficient copper-mediated tandem C(sp2)-H amination to provide quinazolinones from N-(quinolin-8-yl)benzamide and amidine hydrochlorides has been developed. It can afford rather complex products in a single step synthesis from easily availab

Aryne Multicomponent Reactions by Directed C?H Activation

Arylation via ortho C?H activation by the aid of directing groups has been explored recently by many researchers. Herein, a palladium-catalyzed C?H arylation using 8-aminoquinoline as a bidentate directing group has been developed. The reaction furnishes only C?H arylation, unlike previous methods where cyclization to corresponding isoquinolones is observed. More interestingly, sequential C?H functionalization was observed when methylacrylate and acrylonitrile was added; this led to C?H olefination with the aryl group, which was installed from the aryne precursor.

Rh-Catalyzed General Method for Directed C-H Functionalization via Decarbonylation of in-Situ-Generated Acid Fluorides from Carboxylic Acids

A Rh-catalyzed decarbonylative C-H coupling of in-situ-generated acid fluorides with amide substrates bearing ortho-Csp2-H bonds has been developed. This method enables alkyl, aryl, and alkenyl carboxylic acids to undergo decarbonylative coupling with C-H bonds of (hetero)aromatic or alkenyl amides in generally good yields via the in situ conversion of carboxylic acids into acid fluorides and also allows for the functionalization of a series of structurally complex carboxyl-containing natural products and pharmaceuticals as well as pharmaceutical amide derivatives.

Regioselective remote C5 cyanoalkoxylation and cyanoalkylation of 8-aminoquinolines with azobisisobutyronitrile

The efficient regioselective C-H cyanoalkoxylation and cyanoalkylation of 8-aminoquinoline derivatives at the C5 position have been achieved under O2 and N2 atmospheres, respectively. Using 2,2′-azobisisobutyronitrile (AIBN) as a radical precursor, the pr

Copper/Silver Cocatalyzed Regioselective C5-H Functionalization of 8-Aminoquinoline Amides with 1,3-Dicarbonyl Compounds

A copper/silver co-catalyzed cross-dehydrogenative coupling reaction is developed to achieve exclusively remote C5-H coupling of 8-aminoquinoline amides with the methylenic sp 3 C-H bond of 1,3-dicarbonyl compounds. This protocol provides a hig

Rhodium-Catalyzed Alkylation of C?H Bonds in Aromatic Amides with Non-activated 1-Alkenes: The Possible Generation of Carbene Intermediates from Alkenes

The alkylation of C?H bonds (hydroarylation) in aromatic amides with non-activated 1-alkenes using a rhodium catalyst and assisted by an 8-aminoquinoline directing group is reported. The addition of a carboxylic acid is crucial for the success of this reaction. The results of deuterium-labeling experiments indicate that one of deuterium atoms in the alkene is missing, suggesting that the reaction does not proceed through the commonly accepted mechanism for C?H alkylation reactions. Instead the reaction is proposed to proceed through a carbene mechanism. The carbene mechanism is also supported by preliminary DFT calculations.

Synthesis of diaryl sulfides through C–H bond functionalization of arylamides with cobalt salt and elemental sulfur

A cobalt(II)-mediated, highly chemoselective thioarylation reaction of arylamides with elemental sulfur was reported. This reaction led to the formation of various symmetric diaryl sulfides in yields of up to 65% under mild reaction conditions. A cobalt-sulfur radical process was proposed based on preliminary results and mechanistic studies.

Synthesis of phthalic acid derivatives: Via Pd-catalyzed alkoxycarbonylation of aromatic C-H bonds with alkyl chloroformates

A Pd(ii)-catalyzed alkoxycarbonylation of aromatic C-H bonds with alkyl chloroformates has been developed. A broad range of benzamides and alkyl chloroformates are compatible with this protocol. The reaction is operationally simple and scalable. The direct group could be readily removed to access substituted phthalic acid esters (PAEs), 1,2-dibenzyl alcohols and phthalamides. Besides alkoxycarbonylation of benzamide β-C-H bonds, γ-alkoxycarbonylation of 2-phenylacetamide is also feasible.

Silver(I)-Catalyzed C-X, C-C, C-N, and C-O Cross-Couplings Using Aminoquinoline Directing Group via Elusive Aryl-Ag(III) Species

Cross-coupling transformations are a powerful tool in organic synthesis. It is known that this kind of transformation undergoes 2-electron redox processes, and, for this reason, silver has been nearly forgotten as catalyst for cross-couplings because silver is mainly considered as a 1-electron redox metal. Herein, we disclose effective Ag(I)-catalyzed cross-coupling transformations using bidentate aminoquinoline as a directing group toward different nucleophiles to form C-C, C-N, and C-O bonds. DFT calculations indicate the feasible oxidative addition of L1-I substrate via the Ag(I)/Ag(III) catalytic cycle. Furthermore, ion spectroscopy experiments suggest a highly reactive aryl-Ag(III) that in the absence of nucleophiles reacts to form an intermolecular cyclic product [5d-Ag(I)-CH3CN], which in solution forms 5a. This work proves that silver can undergo 2-electron redox processes in cross-coupling reactions like Pd and Cu.

Cobalt(II)-Catalyzed Acyloxylation of C-H Bonds in Aromatic Amides with Carboxylic Acids

The cobalt(II)-catalyzed acyloxylation of C-H bonds in aromatic amides containing an 8-aminoquinoline moiety as the directing group with carboxylic acids is reported. Various carboxylic acids including aromatic and aliphatic carboxylic acids are applicable to the reaction. The reaction displays a broad substrate scope and high functional group tolerance. The reaction is carried out under air.