80818-45-7

Upstream product

• 78-38-6 ethylphosphonic acid diethyl ester 
• 100-52-7 benzaldehyde 
• 103-71-9 phenyl isocyanate 
• 35086-87-4 (E)-2-methyl-3-phenylacryloyl chloride 
• 62-53-3 aniline 
• 620-71-3 N-(phenyl)-2-methylacetamide 
• 100-51-6 benzyl alcohol 
• 1895-97-2 2-methyl-3-phenylacrylic acid 
• 673-32-5 1-Phenylprop-1-yne 
• 1611-83-2 2-methyl-N-phenylacrylamide 
• 108-90-7 chlorobenzene 
• 38449-13-7 2-methyl-3-phenylacryloyl chloride 

Downstream Products

• 6085-89-8 2-methyl-3,N-diphenyl-propionamide 
• 586965-33-5 C₁₆H₁₇NO 
• 1351464-70-4 C₁₉H₂₁NO 
• 135578-99-3 (2E)-N,2-dimethyl-N,3-diphenylacrylamide 
• 2721-59-7 3-methylcarbostyril 
• 57876-69-4 2-chloro-3-methyl-quinoline 

Relevant academic research and scientific papers

Versatile One-Pot Synthesis of Polysubstituted Cyclopent-2-enimines from α,β-Unsaturated Amides: Imino-Nazarov Reaction

The imino-Nazarov cyclization of the polysubstituted pentan-1,4-diene-3-imines was realized. To this aim, a one-pot procedure involving reductive alkenyliminylation of α,β-unsaturated secondary amides with potassium organotrifluoroborates, followed by acid-catalyzed imino-Nazarov cyclization of the polysubstituted pentan-1,4-diene-3-imine intermediates, was studied systematically. This mild, operationally simple, flexible, and high-yielding protocol efficiently affords polysubstituted pentan-1,4-diene-3-imines, cyclopentenimines, and α-amino cyclopentenones, which are useful scaffolds in organic synthesis. The substituent effect at the C2 position of the polysubstituted pentan-1,4-diene-3-imines was studied by means of density-functional theory calculations. Results suggested that the electron-donating group facilitates the imino-Nazarov cyclization process.

Manganese(I) Catalyzed α-Alkenylation of Amides Using Alcohols with Liberation of Hydrogen and Water

Herein, unprecedented manganese-catalyzed direct α-alkenylation of amides using alcohols is reported. Aryl amides are reacted with diverse primary alcohols, which provided the α,β-unsaturated amides in moderate to good yields with excellent selectivity. Mechanistic studies indicate that Mn(I) catalyst oxidizes the alcohols to their corresponding aldehydes and also plays an important role in efficient C═C bond formation through aldol condensation. This selective olefination is facilitated by metal-ligand cooperation by the aromatization-dearomatization process operating in the catalytic system. Biorenewable alcohols are used as alkenylation reagents for the challenging α-alkenylation of amides with the highly abundant base metal manganese as a catalyst, which results in water and dihydrogen as the only byproduct, making this catalytic transformation attractive, sustainable, and environmentally benign.

Titanium-Promoted Cross-Coupling for the Selective Synthesis of Polysubstituted, Conjugated Amides

α,β-Unsaturated amides are important building blocks and are key structural elements in a number of biologically active natural products. Despite their importance and prevalence, few methods exist to prepare conjugated amides directly and modularly. To address this gap, a titanium-promoted coupling of alkynes and isocyanates has been developed. The method is highly stereoselective, producing only the E isomer with good chemoselectivity and regioselectivity (>95/5), for unsymmetrical internal alkynes that contain a steric bias. The reactive titanacyclopentene intermediate formed from the coupling of the alkyne and isocyanate was additionally reacted with various electrophiles to access tetrasubstituted enamides.

Fragment-Based Discovery of Low-Micromolar ATAD2 Bromodomain Inhibitors

Overexpression of ATAD2 (ATPase family, AAA domain containing 2) has been linked to disease severity and progression in a wide range of cancers, and is implicated in the regulation of several drivers of cancer growth. Little is known of the dependence of

Metal-free synthesis of 3,3-disubstituted oxoindoles by iodine(III)-catalyzed bromocarbocyclizations

"I" did it: An iodine(III)-mediated bromocarbocyclization was elaborated as an efficient tool for the synthesis of oxoindoles. This method is applicable to a variety of structurally different substrates, also with chemically sensitive groups, and gives access to the heterocycles in a regio- and stereoselective fashion (see scheme). The indole-2-ones obtained can be converted easily into structurally complex target compounds, such as the alkaloid physostigmine. Copyright

An efficient and general method for the heck and buchwald-hartwig coupling reactions of aryl chlorides

The β-diketiminatophosphane Pd complex acted as a powerful catalyst for the Heck coupling of aryl chlorides with alkenes. Various aryl and heteroaryl chlorides were coupled efficiently under relatively mild conditions. Furthermore, this catalytic system also proved to be highly active in the Buchwald-Hartwig coupling of deactivated and sterically hindered aryl chlorides at room temperature.

Highly enantioselective construction of the α-chiral center of amides via iridium-catalyzed hydrogenation of α,β-unsaturated amides

The chiral center at the a-position of amides is installed in excellent enantioselectivity via the iridium-catalyzed asymmetric hydrogenation of αβ-unsaturated amides under mild conditions. Even aliphatic amides are suitable substrates. The presence of a

PHOSPHONATES α-LITHIES, AGENTS DE TRANSFERT FONCTIONNEL. PREPARATION DE PHOSPHONATES α-AMIDES ET D'AMIDES α,β-INSATURES, α-SUBSTITUES

Lithiated anions (9) or (10) of secondary or tertiary α-amidophosphonates are prepared either by reaction between an α-phosphonyl carbanion and an isocyanate or a carbamate (first strategy), or by condensation of an amide enolate with diethylchlorophosphate (second strategy).Acidic hydrolysis of (9) or (10) gives α-amidophosphonate (1) alkylated or not in the α-position. (9) and (10) react with aromatic or aliphatic aldehydes to produce α,β-unsatured secondary or tertiary amides (2).

Selective Reduction of αβ-Olefinic Amides and Lactams by Magnesium and Methanol

αβ-Olefinic amides with various substitution patterns at the carbon-carbon double bond and at nitrogen are all reduced to the corresponding saturated amides by magnesium and methanol.The same reducing system reduces N-benzyl-8-azabicyclonona-1(6),3-dien-7-ones at the conjugated double bond to give mixtures of the cis- and trans-dihydro-derivatives; the isolated, non-conjugated double bond is not reduced, even in the 3,4-diphenylsubstituted compound.Magnesium and methanol reduces quinolin-2(1H)-ones to their 3,4-dihydro-derivatives, and 5,6,7,8-tetrahydroquinolin-2(1H)-one to a mixture of two dihydro-derivatives.