4242-46-0

Usage

Synthesis Reference(s)

Synthesis, p. 1054, 1986 DOI: 10.1055/s-1986-31873

InChI:InChI=1/C15H11NO2/c16-11-14(12-7-3-1-4-8-12)18-15(17)13-9-5-2-6-10-13/h1-10,14H

Upstream product

• 613-90-1 benzoyl cyanide 
• 532-28-5 (RS)-mandelonitrile 
• 74-90-8 hydrogen cyanide 
• 10425-22-6 Benzil dicyanohydrin 
• 100-52-7 benzaldehyde 
• 151-50-8 potassium cyanide 
• 98-88-4 benzoyl chloride 
• 134-81-6 benzil 
• 108-94-1 cyclohexanone 
• 122-78-1 phenylacetaldehyde 
• 2408-36-8 lithium cyanide 
• 116944-02-6 6-benzoyl-6,7-dihydro-3-phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine-7-carbonitrile 
• 116944-04-8 6-benzoyl-6,7-dihydro-5-methyl-3-phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine-7-carbonitrile 
• 67-64-1 acetone 

Downstream Products

• 36715-43-2 1-(furan-2-yl)-2-hydroxy-2-phenylethanone 
• 93-89-0 benzoic acid ethyl ester 
• 120-51-4 benzoic acid benzyl ester 
• 1459-20-7 1,2-diphenyl-2-oxoethyl benzoate 
• 73981-13-2 2-ethoxy-2-oxo-1-phenylethyl benzoate 
• 64649-52-1 benzoyloxy-phenyl-acetic acid amide 
• 38828-29-4 α-benzoyloxy-4-methoxy-deoxybenzoin 
• 38828-30-7 4-Methoxybenzoin benzoate 
• 90921-64-5 (4,5-dihydro-thiazol-2-yl)-phenyl-methanol 
• 89549-77-9 Benzoic acid cyano-phenyl-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methyl ester 
• 603-35-0 triphenylphosphine 
• 102034-67-3 2-benzoyloxy-2(4-bromophenyl)-1-phenylethanone 
• 90904-37-3 methyl α,β-dibenzoyl-propionate 
• 55-21-0 benzamide 

Relevant academic research and scientific papers

Alkyl phosphines promoted reductive coupling of acyl cyanides: formation of O-acyl cyanohydrins

The reductive coupling of acyl cyanides promoted by alkyl phosphines has been discovered. Under mild reaction conditions, the substituted cyanohydrins were obtained in moderate to high yields by using trimethylphosphine or tributylphosphine as a promoter.

Palladium-catalyzed C-H activation of simple arenes and cascade reaction with nitriles: access to 2,4,5-trisubstituted oxazoles

An efficient and straightforward protocol for the assembly of the pharmaceutically and biologically valuable oxazole skeleton is achieved for the first time from readily available simple arenes and functionalized aliphatic nitriles. This transformation in

Synthesis of Imidazoles and Oxazoles via a Palladium-Catalyzed Decarboxylative Addition/Cyclization Reaction Sequence of Aromatic Carboxylic Acids with Functionalized Aliphatic Nitriles

We herein report an efficient approach for the assembly of multiply substituted imidazoles and oxazoles in a single-step manner. These transformations are based on a decarboxylation addition and annulation of readily accessible aromatic carboxylic acids a

Divergent Palladium-Catalyzed Tandem Reaction of Cyanomethyl Benzoates with Arylboronic Acids: Synthesis of Oxazoles and Isocoumarins

A palladium-catalyzed tandem reaction of cyanomethyl benzoates with arylboronic acids has been achieved. Substitution at the 2-position of cyanomethyl benzoates was found to be crucial for the selective synthesis of oxazoles and isocoumarins. Cyanomethyl

Synthesis of 2,4,5-Trisubstituted Oxazoles via Pd-Catalyzed C-H Addition to Nitriles/Cyclization Sequences

A practical and flexible intermolecular protocol for the diverse synthesis of trisubstituted oxazole derivatives via a Pd-catalyzed direct C-H addition of electronic-rich heteroarenes to O-acyl cyanohydrins bearing an α-hydrogen/cyclization sequence is described. A wide range of trisubstituted oxazoles can be prepared from readily available starting materials in good to high yields with high efficiency under redox neutral reaction conditions.

Synthesis of benzoyl cyanide through aerobic photooxidation of benzyl cyanide using carbon tetrabromide as a catalyst

We developed a synthetic method toward benzoyl cyanide through aerobic photooxidation of benzyl cyanide in the presence of carbon tetrabromide under visible light irradiation with fluorescent lamps.

Direct synthesis of cyanohydrin esters from aroyl chlorides using potassium hexacyanoferrate(II) as an eco-friendly cyanide source

Abstract A direct synthetic method for cyanohydrin esters from aroyl chlorides using potassium hexacyanoferrate(II) as an eco-friendly cyanide source and tributylphosphine as a promoter is described. This protocol has advantages of no use of strong toxic cyanating agents, high yield, and simple work-up procedure.

Titanium-mediated addition of grignard reagents to acyl cyanohydrins: Aminocyclopropane versus 1,4-diketone formation

The 1,2-dianion reactivity of the reagent generated from EtMgBr and titanium isopropoxide was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples), giving both aminocyclopropane derivatives and 1,4-dicarbonyl compounds. When the reaction was performed in diethyl ether, 5-hydroxy-1,4-diketones were the main product. Under specific conditions (use of tetrahydrofuran and a bulky carboxylic moiety), the cyclopropane derivatives were obtained in good yields. The observed dichotomy may be explained by a ring-opening of the five-membered titanacycle intermediate followed by a nonselective acyl addition. The 1,2-dianion reactivity of the reagent generated from EtMgBr and Ti(OiPr)4 was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples). When the reaction was performed in diethyl ether, 1,4-diketones were mainly isolated. Under certain conditions, cyclopropane derivatives were also obtained in good yields. A mechanism rationalizing this dichotomy is presented. Copyright

Cyanative self-condensation of aromatic aldehydes promoted by VO(O iPr)3-Lewis base as a cooperative catalyst

Self-condensation of aromatic aldehydes with trimethylsilyl cyanide proceeded by the cooperative catalytic effect of VO(OiPr)3 and a Lewis base to give the corresponding O-acylated cyanohydrins. The reaction conversion and selectivity were strongly dependent on the solvent used, the Lewis base, and the presence of oxygen. All the nine kinds of aromatic aldehydes considered herein afforded the O-acylated cyanohydrins with excellent selectivity under an O2 atmosphere.

Mechanistic studies on the enantioselective BINOLAM/titanium(IV)-catalyzed cyanobenzoylation of aldehydes: Part 1

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