37864-30-5

Upstream product

• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 100-52-7 benzaldehyde 
• 611-73-4 Benzoylformic acid 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 7473-98-5 2-hydroxy-2-methylpropiophenone 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 52562-19-3 2-isopropenylaniline 
• 108-88-3 toluene 
• 53599-95-4 N-benzoyl-4-methyl-1,2-dihydroquinaldonitrile 

Relevant academic research and scientific papers

Visible-Light-Induced Decarboxylative Acylation of Pyridine N-Oxides with α-Oxocarboxylic Acids Using Fluorescein Dimethylammonium as a Photocatalyst

Herein, the development of a visible-light-induced catalytic system to achieve the decarboxylative acylation of pyridine N-oxides with α-oxocarboxylic acids, at room temperature and using the organic dye fluorescein dimethylammonium as a new type of photocatalyst, is reported. A series of 2-arylacylpyridine N-oxides were selectively synthesized in moderate to good yields by controlling the polarity of the reaction solvent. The developed strategy was successfully applied in the synthesis of an important intermediate of the drug, acrivastine, on a gram scale. Notably, this is the first time that fluorescein dimethylammonium has been used to catalyze the Minisci-type C?H decarboxylative acylation reaction. The mechanism of decarboxylative acylation was studied by capturing adducts of acyl radicals and 1,1-diphenylethylene to confirm a radical mechanism. The disclosed catalytic system provides a green synthetic strategy for decarboxylative acylation without the use of additional oxidants or metal catalysts. (Figure presented.).

Surgical Cleavage of Unstrained C(sp3)?C(sp3) Bonds in General Alcohols for Heteroaryl C?H Alkylation and Acylation

We reported herein a predictable and surgical cleavage of carbon-carbon bond in alcohols. A wide range of 1°, 2° and 3° alcohols including sugars and steroids without ring strain or steric hindrance were all compatible with this system. Also it offered a green and practical strategy for generation of alkyl/acyl radicals using alcohols as the sources. Besides, the features of visible-light-initiation, catalyst and metal free, excellent selectivity and mild conditions make it valuable and attractive. (Figure presented.).

RuII-Catalyzed/NH2-Assisted Selective Alkenyl C-H [5 + 1] Annulation of Alkenylanilines with Sulfoxonium Ylides to Quinolines

A novel ruthenium-catalyzed [5 + 1] annulation of 2-alkenylanilines with sulfoxonium ylides was developed for the rapid assembly of highly functionalized quinolines. This new catalytic process employs challenging but synthetically ideal free amino functionality to achieve alkenyl C-H activation with sulfoxonium ylides as one-carbon coupling partners. Various 2-acylquinolines could be obtained with good yields and excellent functional group tolerance. Moreover, the potential synthetic application of this methodology was exemplified by several chemical transformations.

Photoredox-Catalyzed Decarboxylative C-H Acylation of Heteroarenes

A mild, environmentally friendly, and regioselective acylation of heterocycles with inexpensive carboxylic acids is reported via photoredox catalysis. The strategy is highlighted with good functional group tolerance and substrate scope which could rapidly

Synthesis method of acylated quinoline or isoquinoline derivative

The invention discloses a synthesis method of an acylated quinoline or isoquinoline derivative, belongs to the field of organic synthesis, and aims to solve the problems of complicated reaction, severe conditions and low environmental friendliness in the

Iridium-Catalyzed Highly Enantioselective Transfer Hydrogenation of Aryl N-Heteroaryl Ketones with N-Oxide as a Removable ortho-Substituent

A highly enantioselective transfer hydrogenation of non-ortho-substituted aryl N-heteroaryl ketones, using readily available chiral diamine-derived iridium complex (S,S)-1f as a catalyst and sodium formate as a hydrogen source in a mixture of H2O/i-PrOH (v/v = 1:1) under ambient conditions, is described. The chiral aryl N-heteroaryl methanols were obtained with up to 98.2% ee by introducing an N-oxide as a removable ortho-substituent. In contrast, no more than 15.1% ee was observed in the absence of an N-oxide moiety. Furthermore, the practical utility of this protocol was also demonstrated by gram-scale asymmetric synthesis of bepotastine besilate in 51% total yield and 99.9% ee.

TBHP/TFA mediated oxidative cross-dehydrogenative coupling of N-heterocycles with aldehydes

An effective and metal-free oxidative cross-dehydrogenative coupling (CDC) of N-heterocycles with diverse aldehydes has been established in the presence of TBHP/TFA. The scope with respect to aldehyde and N-heterocycle components is broad, allowing facile synthesis of a broad range of structurally diverse C1-acyl substituted heterocycles in good efficiency.

Polar effects in free-radical reactions. A novel homolytic acylation of heteroaromatic bases by aerobic oxidation of aldehydes, catalysed by N-hydroxyphthalimide and Co salts

A new process for the homolytic acylation of protonated heteroaromatic bases is described; an N-oxyl radical (PINO) generated from N-hydroxyphthalimide by air oxygen and Co(II) abstracts a hydrogen atom from an aldehyde. The resulting nucleophilic acyl radical adds to a heteroaromatic base, which is then rearomatised in a chain process. Quinazoline has an anomalous behaviour, giving 3H-quinazolin-4-one as the only reaction product.

Radical Decarboxylative Alkylation onto Heteroaromatic Bases with Trivalent Iodine Compounds

Heteroaromatic bases containing nitrogen atoms were easily alkylated with carboxylic acids in the presence of benzene and pentafluorobenzene via radical pathways.Similarly, the alkylation onto heteroaromatic bases was carried out with oxalic acid monoalkyl esters, which were prepared from alcohols and oxalyl dichloride, in the presence of the same trivalent iodine compounds.Moreover, this system was applied to the synthesis of C-nucleosides with the carboxylic acids bearing a sugar moiety.

FACILE RADICAL DECARBOXYLATIVE ALKYLATION OF HETEROAROMATIC BASES USING CARBOXYLIC ACIDS AND TRIVALENT IODINE COMPOUNDS

Many kinds of heteroaromatic bases were easily alkylated by the reaction of carboxylic acids with benzene or pentafluorobenzene via radical decarboxylative pathways.This system was further applied to the reaction with tetrahydrofurylcarboxylic acid, 1-(2,3,5-tri-O-benzyl)-D-ribofuranosylacetic acid, and 1-(2,3,5-tri-O-benzyl)-D-ribofuranosylcarboxylic acid for the model synthesis of C-nucleosides.