51765-79-8

Upstream product

• 590-17-0 cyanomethyl bromide 
• 94287-27-1 tert-butyldimethyl((1-phenylprop-1-en-1-yl)oxy)silane 
• 107-14-2 chloroacetonitrile 
• 4786-20-3 but-2-enenitrile 
• 100-52-7 benzaldehyde 

Downstream Products

• 7315-67-5 3-methyl-4-oxo-4-phenylbutanoic acid 
• 101073-95-4 ethyl 3-methyl-4-phenyl-4-butanoate 
• 101073-98-7 methyl 3-methyl-4-phenyl-4--butanoate 
• 110766-33-1 5-methyl-6-phenyl-4,5-dihydro-2H-pyridazin-3-one 
• 40394-84-1 3-Methyl-4-oxo-4-phenyl-butansaeure-ethylester 

Relevant academic research and scientific papers

A Photochemical Organocatalytic Strategy for the α-Alkylation of Ketones by using Radicals

Reported herein is a visible-light-mediated radical approach to the α-alkylation of ketones. This method exploits the ability of a nucleophilic organocatalyst to generate radicals upon SN2-based activation of alkyl halides and blue light irradiation. The resulting open-shell intermediates are then intercepted by weakly nucleophilic silyl enol ethers, which would be unable to directly attack the alkyl halides through a traditional two-electron path. The mild reaction conditions allowed functionalization of the α position of ketones with functional groups that are not compatible with classical anionic strategies. In addition, the redox-neutral nature of this process makes it compatible with a cinchona-based primary amine catalyst, which was used to develop a rare example of enantioselective organocatalytic radical α-alkylation of ketones.

Synthetic utility of stannyl enolates as radical alkylating agents

(Equation presented) The radical-initiated β-ketoalkylation of haloalkanes with tributylstannyl enolates is described. Stannyl enolates derived from aromatic ketones are reactive toward the homolytic β-ketoalkylation of simple haloalkanes as well as those activated by an electron-withdrawing group. The reactivity of stannyl enolates as radical alkylating agents can be utilized for an efficient three-component coupling reaction among stannyl enolates, haloalkanes, and electron-deficient alkenes.

PREPARATION AND REACTIONS OF SOME 2-THIENYL AND 3-THIENYL PYRIDAZINONES AND PYRIDAZINES

The preparation and reactions of some pyridazinone derivatives with 2- and 3-thienyl substituents are described.Precursor 4-oxobutanoic acids Ar2COCH2CH(Ar1)CO2H (Ar1=Pb, Ar2=2-thienyl and Ar1=2-thienyl, Ar2=Pb) were obtained by addition of HCN to the chalcones Ar1CH=CHCOAr2 followed by acid hydrolysis of the resulting nitrile.Nitriles, ArCOCH(CH3)CH2CN were prepared by the Michael-Stetter reaction and converted via the acids to the 4,5-dihydropyridazin-3(2H)-ones.Two methods wereused to obtain pyridazin-3(2H)-ones viz oxidation of the 4,5-dihydro derivatives with selenium dioxide and base-catalyzed condensation of methanal or aryl aldehydes at the 4-position of the 4,5-dihydro compound.

Process for preparing ketones

Ketones are prepared by reacting an aromatic or heterocyclic aldehyde in the presence of a cyanide ion with an unsaturated compound having the formula (I): STR1 wherein R1, R2 and R3 are the same or different and are selected from the group of hydrogen, optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic, heterocyclic and carboxylic acid ester and R4 is nitrile (CN), --CO--R5 or --CO--OR5 wherein R5 is selected from the group of optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic and heterocyclic and R1 and R2 and/or R1 and R3 and/or R2 and R5 or R3 and R5 together with the carbon atoms to which they are attached as substituents may also form a carbocyclic or heterocyclic ring. Ketones prepared according to the process of the invention have the formula: STR2 wherein R1 ' and R3 ' are identical or different and are selected from the group of hydrogen, lower alkyl having up to 3 C-atoms and optionally substituted phenyl; and R6 ' is optionally substituted phenyl or a pyridyl.