25559-56-2

Upstream product

• 2009-96-3 2-diazo-1-phenylbutane-1,3-dione 
• 62-53-3 aniline 
• 103-71-9 phenyl isocyanate 
• 1450-07-3 1-benzoylethylidenetriphenylphosphorane 
• 10488-87-6 ethyl 2-benzoylpropionate 
• 14088-57-4 2-diazo-1-phenyl-1-propanone 
• 201230-82-2 carbon monoxide 
• 66981-69-9 2-(Dimethyl-λ⁴-sulfanylidene)-1-phenyl-propan-1-one 
• 622-37-7 Phenyl azide 
• 99408-66-9 3,5-diphenyl-4-aza-2,4-heptadiene 
• 116916-23-5 2-methyl-3-(1-phenylpropylamino)-N,3-diphenylprop-2-enamide 
• 93-55-0 1-phenyl-propan-1-one 
• 124982-28-1 3-methyl-N-phenyl-4-phenyl-2,4-dioxobutyramide 
• 29047-30-1 α-Methyl-β-methylthiomethoxy-β-phenylacryl-anilid 

Downstream Products

• 93-89-0 benzoic acid ethyl ester 
• 111528-58-6 2-methyl-3-phenyl-3-propoxy-acrylic acid anilide 
• 620-71-3 N-(phenyl)-2-methylacetamide 
• 65-85-0 benzoic acid 
• 1422194-20-4 C₁₆H₁₅NO₃ 
• 37118-75-5 3-methyl-4-phenyl-2-quinolinone 

Relevant academic research and scientific papers

Unique features of chiral palladium enolates derived from β-ketoamide: structure and catalytic asymmetric Michael and fluorination reactions

Abstract We have previously reported enantioselective reactions of 1,3-diketones and β-ketoesters with various electrophiles catalyzed by chiral Pd complex, in which chiral Pd enolates play a key role. Here, we present a detailed examination of Pd-catalyz

Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds

Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds provides a simple and atom-economical approach toward enamides and isoquinolones. This paper reports two catalyst systems for these transformations which employ iron(ii) complexes [Fe(dpbz)]Br2 (dpbz = 1,2-bis(diphenylphosphino)benzene) and FeBr2/Et3N, respectively. [Fe(dpbz)]Br2 was found to be highly effective at converting 2-azido-2,3-dihydro-1H-inden-1-ones to isoquinolones. The reagent combination of FeBr2/Et3N, on the other hand, exhibited a broader catalytic scope, owing to the beneficial effect of Et3N. This latter catalyst system enables 2-azido-2-methyl-1,3-dicarbonyl compounds to be converted to the corresponding enamides under mild conditions in good yields.

Enantioselective α-hydroxylation of -ketoamides

The first enantioselective α-hydroxylation reaction of α-substituted -ketoamides has been developed by using the commercially available hydroquinine/TBHP system. The tertiary alcohols are obtained in good to high yield and up to 83% ee, which can be improved by a single crystallization.

Pd-catalyzed carbonylation of diazo compounds at atmospheric pressure: A catalytic approach to ketenes

The carbonylation of carbenes through catalytic cycles is highly desirable due to the importance of ketene-mediated reactions in organic synthesis. In this investigation, a highly efficient and mild catalytic approach toward ketene intermediates has been developed based on Pd-catalyzed carbonylation of diazo compounds with CO. When α-diazocarbonyl compounds or N-tosylhydrazone salts are heated in the presence of a palladium catalyst under atmospheric pressure of CO, ketene intermediates are formed in situ, where they undergo further reactions with various nucleophiles such as alcohols, amines, or imines. The Pd-catalyzed tandem carbonylation-Staudinger cycloaddition gives β-lactam derivatives in good yields with excellent trans diastereoselectivity. The results from DFT calculation on the reaction mechanism suggest that Pd is involved in the [2 + 2] cycloaddition process and affects the diastereoselectivity of the β-lactam products by assisting isomerization of the addition intermediate. On the other hand, the acylketenes generated from the Pd-catalyzed carbonylation of α-diazoketones react with imines in a formal [4 + 2] cycloaddition manner to afford 1,3-dioxin-4-one derivatives. This straightforward carbonylation provides a new approach toward highly efficient catalytic generation of ketene species under mild conditions.

Cycloaddition of Unactivated 2-Aza-1,3-dienes with Heterocumulenes: A Convenient Route to the Synthesis of 1,3-Difunctionalized Compounds

The cycloaddition of unactivated 2-aza-1,3-dienes (2) with isocyanates and isothiocyanates (3) gives with complete regio- and chemo-selectivity 1,2-dihydropyrimidin-4(3H)-ones and -thiones (4).This is the first example of a cycloaddition of unactivated 2-

A NEW SYNTHESIS OF β-KETO AMIDES VIA REACTION OF KETONE LIZHIUM ENOLATES WITH ISOCYANATES

A series of β-ketoamides was prepared by a convenient new method involving addition of various isocyanates to lithium enolates of acetophenone propiophenone and pinacolone.

Synthesis of β-Ketocarboxamide Derivatives Using 2,2-Dimethyl-2H,4H-1,3-dioxin-4-ones

Thermal reaction of 2,2-dimethyl-2H,4H-1,3-dioxin-4-ones (1) with amines was studied.Acylketenes 2, generated by heating of 1, reacted with anilines and benzylamine to give the corresponding β-ketocarboxamides (3,4, and 5) in good yields.The reaction of 1 with ammonia gave 3-amino-2-alkenamides (7), which were hydrolyzed to β-ketocarboxamides (6).The former products 7 were readily transformed to the 6-substituted 2-methyl-3H-pyrimidin-4-ones (9) via the 3-acetamido-2-alkenamides (8).Acylation of O-benzylhydroxylamine with 1 gave the β-ketohydroxamic acids 10.Debenzylation of 10 followed by cyclization gave rise to 5-alkyl-3-hydroxyisoxazoles (12).The reaction of 1 with amides gave the corresponding N-acetylated amides (13). Keywords --- 2H,4H-1,3-dioxin-4-one; thermal fragmentation; acylketene; acylation; carboxamide; hydroxamic acid; 3-hydroxyisoxazole; 3H-pyrimidin-4-one

Reactions with Phosphine Alkylenes, XLIII. A General Synthesis for α-Branched β-Ketocarboxylic Acid Anilides

α-Acylphosphonium ylides 5 react with phenylisocyanate (7) with formation of α-acylketeneimines 8 which can be hydrolysed to α-branched β-ketocarboxylic acid anilides 9.