95496-05-2

Upstream product

• 32830-97-0 1-chloro-3-pentanone 
• 62-53-3 aniline 
• 1629-58-9 4-penten-3-one 
• 7732-18-5 water 
• 622-79-7 benzyl azide 
• 78-93-3 butanone 
• 538-51-2 benzylidene phenylamine 
• 78-94-4 methyl vinyl ketone 
• 616-25-1 1-Penten-3-ol 
• 598-32-3 2-hydroxy-3-butene 
• 64-19-7 acetic acid 

Downstream Products

• 19020-26-9 4-ethylquinoline 

Relevant academic research and scientific papers

Rhodium catalyzed multicomponent dehydrogenative annulation: one-step construction of isoindole derivatives

A strategy for one-pot synthesis of isoindoles is describedviaa catalytic multicomponent dehydrogenative annulation of diarylimines, vinyl ketones and simple amines. In the presence of a rhodium catalyst and Cu oxidant, four C-H and two N-H bonds are activated along with the formation of one new C-C and two new C-N bonds, leading to a series of isoindole derivatives in good to very high isolated yields.

Palladium-catalyzed aerobic oxidative coupling of allylic alcohols with anilines in the synthesis of nitrogen heterocycles

We report herein an unprecedented and expedient Pd-catalyzed oxidative coupling of allyl alcohols with anilines to afford β-amino ketones which are converted into substituted quinolines in a one-pot fashion. The exclusive preference for N-alkylation over N-allylation makes this approach unique when compared to those reported in literature. Detailed mechanistic investigations reveal that the conjugate addition pathway was the predominant one over the allylic amination pathway. The notable aspects of the present approach are the use of readily available, bench-stable allyl alcohols and molecular oxygen as the terminal oxidant, in the process dispensing the need for unstable and costly enones. Further, we explored the synthetic utility of β-amino ketones through an intramolecular α-arylation methodology and a one-pot domino annulation, thereby providing rapid access to indolines and quinolines.

Copper-Catalyzed Aza-Michael Addition of Aromatic Amines or Aromatic Aza-Heterocycles to α,β-Unsaturated Olefins

A highly efficient and mild Cu-catalyzed conjugate addition reaction of aromatic amines and aromatic aza-heterocycles to α,β-unsaturated olefins is described. The transformation is promoted by 3-7 mol % of a Cu complex generated in situ from a mixture of inexpensive CuCl, a readily available phosphine or imidazolium salt, and KOt-Bu at ambient temperature. A wide range of β-amino sulfone, β-amino nitrile, and β-amino carbonyl compounds is efficiently and selectively synthesized in high yields (62-99%).

Aza-Michael reaction promoted by aqueous sodium carbonate solution

A general and efficient aza-Michael reaction promoted by aqueous sodium carbonate solution has been developed. The reaction has complete mono-alkylation selectivity and proceeds with complete chirality retention for chiral amino esters. With a broad substrate scope, a well-common catalyst and simple operation, the catalytic approach provides a facile, practicable, economical, and environmentally benign method for the synthesis of β-amino carbonyl compounds.

Lithium tetrafluoroborate catalyzed highly efficient inter- and intramolecular aza-Michael addition with aromatic amines

Lithium tetrafluoroborate has been demonstrated for the first time to be an efficient catalyst in intermolecular aza-Michael addition aromatic amines to electron deficient alkenes. Suitability of the same catalyst in intramolecular aza-Michael addition leading 2-aryl-2,3-dihydroquinolin-4(1H) ones has also been described.

Green, efficient and practical Michael addition of arylamines to α,β-unsaturated ketones

The aza-Michael addition of aromatic amines to α,β-unsaturated ketones was carried out effectively at room temperature in good to excellent yields without any catalyst or solvent. It was significant that part of adducts could be collected in almost quanti

Highly efficient aza-Michael reactions of aromatic amines and N-heterocycles catalyzed by a basic ionic liquid under solvent-free conditions

A task-specific basic ionic liquid, [Bmim]OH, has been introduced as a catalyst for the aza-Michael addition of aromatic amines and N-heterocycles to cyclic or acyclic ketones under neat conditions. The catalyst can be recycled for subsequent reactions without any appreciable loss of efficiency.

Reactions of alkyl azides and ketones as mediated by Lewis acids: Schmidt and Mannich reactions using azide precursors

The Lewis acid-promoted reactions of alkyl azides with ketones can afford several products. Chief among these result from a Schmidt-like insertion of the azide into the carbon - carbon bond adjacent to the carbonyl group. Alternatively, an acid-promoted r