119118-42-2

Upstream product

• 5470-96-2 quinoline 2-carbaldehyde 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 98-86-2 acetophenone 
• 91-63-4 2-methylquinoline 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 

Downstream Products

• 52249-51-1 1-phenyl-3-(quinolin-2-yl)propan-1-one 
• 1323153-81-6 (1S,3aS)-1-phenyl-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline 

Relevant academic research and scientific papers

Direct addition of 2-methylazines to aryl glyoxals for the synthesis of α-hydroxy ketones

A catalyst-free protocol for the reaction of 2-methylazines and aryl glyoxal hydrates leading to α-hydroxy ketones bearing azaarene moiety is described. The process is operationally simple and can be applied to a broad range of substrates.

Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues via Ruthenium-Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination

A rapid construction of enantioenriched benzo-fused quinolizidines, indolizidines, and their analogues by ruthenium-catalyzed asymmetric cascade hydrogenation/reductive amination of quinolinyl- and quinoxalinyl-containing ketones has been developed. This

An expedient approach to synthesize fluorescent 3-substituted 4H-quinolizin-4-ones via (η4-vinylketene)-Fe(CO)3 complexes

An efficient and practical methodology for the synthesis of 3-substituted 4H-quinolizin-4-ones using (η4-vinylketene)-Fe(CO)3 complexes as key intermediates has been developed. The advantage of this transformation lies in the use of

Wittig reactions in water media employing stabilized ylides with aldehydes. Synthesis of α,β-unsaturated esters from mixing aldehydes, α-bromoesters, and Ph3P in aqueous NaHCO3

(Chemical Equation Presented) Water is demonstrated to be an effective medium for the Wittig reaction over a wide range of stabilized ylides and aldehydes. Despite sometimes poor solubility of the reactants, good chemical yields normally ranging from 80 to 98% and high E-selectivities (up to 99%) are achieved, and the rate of the reactions in water is unexpectedly accelerated. The efficiency of water as a medium in the Wittig reaction is compared to conventional organic solvents ranging from carbon tetrachloride to methanol. The aqueous Wittig reaction works best when large hydrophobic entities are present, such as aromatic, heterocyclic aromatic carboxaldehydes, and long-chain aliphatic aldehydes with triphenylphosphoranes. The E/Z-isomeric ratio of the Wittig products appears dependent on the electron-accepting/donating capacity and the location of the substituents present in the aromatic ring. The effect of additives, such as benzoic acid, LiCl, and sodium dodecyl sulfate (SDS), on the Wittig reaction has been explored. The Wittig reaction can also be conducted in the presence of acidic entities, such as phenols and carboxylic acids. In addition, large α-substituents in the aliphatic aldehydes do not jeopardize the reaction. It is also demonstrated that hydrates of aldehydes can be used directly in the aqueous Wittig reaction as substrates. The scope of the aqueous Wittig reaction is extended to 24 examples of one-pot mixtures of Ph3P, α-bromoesters, and aldehydes in sodium bicarbonate solution (at 20°C for 40 min to 3 h) to provide Wittig products of up to 99% yield and up to 98% E-selectivity. Since water is inexpensive, extremely easy to handle, and represents no environmental concerns, it should be considered a possible medium for new organic reactions.

Synthesis of functionalized cyclopentenes through catalytic asymmetric [3+2] cycloadditions of allenes with enones

(Chemical Equation Presented) A phosphepine catalyst mediates enantioselective [3+2] cycloadditions of allenes with a variety of β-substituted α,β-unsaturated enones to produce highly functionalized cyclopentenes that contain two contiguous stereocenters (see scheme). Surprisingly, opposite regioisomers are produced as compared to reactions with β-unsubstituted enones.

Water is an efficient medium for Wittig reactions employing stabilized ylides and aldehydes

Water is demonstrated to be an excellent medium for the Wittig reaction employing stabilized ylides and aldehydes. Although the solubility in water appears to be an unimportant characteristic in achieving good chemical yields and E/Z-ratios, the rate of W

Addressing the unusual reactivity of 2-pyridinecarboxaldehyde and 2- quiuolinecarboxaldehyde in base-catalyzed aldol reactions with acetophenone

2-Pyridinecarboxaldehyde and 2-quinolinecarboxaldehyde undergo rapid, tandem aldol-Michael reactions with the lithium, sodium, and potassium enolates of acetophenone at room temperature to give high yields of 3-(2- pyridinyl)-1-phenyl-2-propenone and 3-(2

Quinolineanalogous Chalcones: Wittig Synthesis, 13C-N.M.R. Spectra and Estimation of ?-Constants for the 2-, 3- and 4-Position of Quinoline

The Wittig type reaction of the quinolinealdehydes 2a-c with benzoylmethylentriphenylphosphorane (1) gives stereoselectively the E-configurated quinolineanalogous chalcones 3a-c.These compounds react with methyl iodide to the N-methyl-quinolinium salts 4a