33357-46-9

Upstream product

• 580-22-3 2-aminoquinoline 
• 93-99-2 benzoic acid phenyl ester 
• 1613-37-2 Quinoline N-oxide 
• 55-21-0 benzamide 
• 4461-33-0 benzoyl isocyanate 
• 98-88-4 benzoyl chloride 
• 612-62-4 2-Chloroquinoline 
• 93-58-3 benzoic acid methyl ester 
• 102-96-5 (2-nitroethenyl)benzene 
• 103-82-2 phenylacetic acid 
• 100-47-0 benzonitrile 
• 74944-11-9 2-phenylimidazo[1,2-a]quinoline 
• 25410-17-7 N,N'-Dibenzoylcarbodiimide 
• 134-81-6 benzil 

Downstream Products

• 580-22-3 2-aminoquinoline 

Relevant academic research and scientific papers

Metal-free Deoxygenative 2-Amidation of Quinoline N-oxides with Nitriles via a Radical Activation Pathway

A metal-, base- and reductant-free approach for the efficient synthesis of various N-acylated 2-aminoquinolines was reported. In this work, readily available nitriles are used as the amide source, and methyl carbazate as both the radical activating reagent and oxygen source. This is the first report on the ester-radical-activated highly regioselective addition of nitriles to quinolone N-oxides. This procedure is expected to complement the current methods for functionalization of N-oxides via an electrophilic activation mechanism. (Figure presented.).

Mild and direct conversion of quinoline N-oxides to 2-amidoquinolines with primary amides

A simple, one-pot procedure is described for the direct conversion of quinoline N-oxides to α-amidoquinolines with primary amides. This methodology is complimentary to the Abramovich reaction, which is limited to the introduction of secondary amides via imidoyl chlorides. Although reaction conditions are quite similar, omission of the base is key for successful reaction with primary amides, which were found not to proceed through the intermediacy of an imidoyl chloride but rather through an acyl isocyanate.

Site-Selective Deoxygenative Amination of Azine N-Oxides with Carbodiimides under Catalyst-, Activator-, Base-, and Solvent-Free Conditions

An operationally simple method for synthesizing 2-amino azines via [3+2] dipolar cycloaddition of azine N-oxide with carbodiimide has been demonstrated. The reaction can proceed smoothly under simple heating conditions without any transition metal catalyst, activator, base, and solvent. This transformation demonstrates a broad substrate scope and produces CO2 as the only co-product. The applicability of this method is highlighted by the late-stage modification of bioactive molecules, including quinine, (±)-α-tocopherol, and tryptamine modified quinoline.

Singlet oxygen mediated dual C-C and C-N bond cleavage in visible light

A tandem cleavage of carbon-carbon and carbon-nitrogen bonds in imidazo[1,2-a]pyridines and imidazo[1,2-a]quinolines is reported in the presence of eosin Y and visible light. The ring opening occurs under ambient conditions through singlet oxygen insertio

Copper Catalyzed Oxidative C-C Bond Cleavage of 1,2-Diketones: A Divergent Approach to 1,8-Naphthalimides, Biphenyl-2,2′-dicarboxamides, and N-Heterocyclic Amides

We report here a simple and efficient copper catalyzed oxidative C-C bond cleavage of stable aromatic cyclic-fused and acyclic 1,2-diketones to deliver amides and imides in high yields. This newly developed protocol provides an excellent tool to transform structurally different 1,2-diketones into different products under the same reaction conditions. The key synthetic features of this methodology are the formation of 1,8-naphthalimides and biphenyl-2,2′-dicarboxamide motifs in high yields. The fluorescent studies of 1,8-naphthalimide derivatives were also carried out in order to show the potential application of these scaffolds.

Copper(II)-mediated, carbon degradation-based amidation of phenylacetic acids toward N -substituted benzamides

The unprecedented synthesis of N-aryl substituted benzamides via the assembly of primary amines and phenylacetic acids has been developed in the presence of copper(ii) acetate. This tandem transformation involving carbon-carbon bond cleavage provides a complementary tool with particular application in the synthesis of secondary benzamides.

Ce(III)-catalyzed highly efficient synthesis of pyridyl benzamides from aminopyridines and nitroolefins without external oxidants

An efficient synthesis of a variety of pyridyl benzamides from 2-aminopyridines and nitroolefins is described. This rare-earth-metal-catalyzed reaction provides the corresponding products with broad substrate scope in moderate to excellent yields, in the absence of additives and external oxidants. Water is used as the source of the carbonyl oxygen atom in pyridyl benzamides. Furthermore, 2-substituted oxazolo[4,5-b]pyridines are formed in good yields under the standard conditions when 2-aminopyridin-3-ols are used as the substrates.

TsOH·H2O-mediated: N -amidation of quinoline N -oxides: Facile and regioselective synthesis of N -(quinolin-2-yl)amides

An operationally simple method with 100% atom economy has been developed for the synthesis of various N-(quinolin-2-yl)amides via the TsOH·H2O-mediated N-amidation of quinoline N-oxides using inexpensive and commercially available nitriles as the amidation reagents. Mechanistic exploration suggested that the reaction probably proceeds through an acid-assisted 1,3-dipolar cycloaddition and an N-O bond cleavage followed by a dehydro-aromatization process.

Practical preparation of challenging amides from non-nucleophilic amines and esters under flow conditions

A fast and efficient protocol for the formation of amides from low nucleophilic amines and esters in flow is described. Products were obtained in good to excellent yields and with the advantage of simultaneous mixing of all reagents at once, avoiding steps for intermediate formation. The protocol is also suitable to be combined with ester synthesis, resulting in the preparation of amides in-line from haloarenes. This journal is