51650-27-2

Upstream product

• 140-29-4 phenylacetonitrile 
• 103-79-7 1-phenyl-acetone 
• 114971-31-2 1-phenylpropan-2-one O-acetyl oxime 
• 536-74-3 phenylacetylene 
• 13213-36-0 1-phenylpropan-2-one oxime 
• 108-22-5 Isopropenyl acetate 
• 19690-01-8 1,2-diphenylethanone O-acetyl oxime 
• 32431-36-0 2,3-dimethylisoquinolinium iodide 
• 111241-10-2 2-methyl-3-phenyl-2-phenylacetylamino-propionic acid ethyl ester 

Relevant academic research and scientific papers

Copper-Catalyzed Aza-Sonogashira Cross-Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles

Nitrogen-substituted alkynes, such as ynamines and ynamides, are versatile synthetic building blocks. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper-catalyzed synthesis of ynimines from readily available O-acetyl ketoximes and terminal alkynes. A wide range of O-acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross-coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.

Rh-catalyzed sequential oxidative C-H activation/annulation with geminal-substituted vinyl acetates to access isoquinolines

The concise synthesis of 3-substituted or non-C3-substituted isoquinolines through Rh-catalyzed sequential oxidative C-H activation/annulation with geminal-substituted vinyl acetates was developed with good functional group tolerance. The protocol was successfully applied to the total synthesis of the natural product papaverine.

REACTION OF BENZYL KETONES WITH NITRILES IN PRESENCE OF POCl3

The reaction of benzyl ketones with nitriles in presence of POCl3 has been examined.It has been found that intermediate N-styrylimidoyl dichlorophosphates formed under reaction conditions undergo further reactions to isoquinoline and pyrimidine derivatives and form the products of fragmentation and condensation.The effect of structure of the substrates on the relative ratios of the products formed has been discussed.