40570-74-9

Usage

Type of compound

Organic compound

Common uses

Synthesis of pharmaceuticals and other fine chemicals

Physical state at room temperature

Yellow crystalline solid

Solubility

Soluble in most organic solvents

Applications

Building block for the preparation of other chemical compounds

Field of use

Organic chemistry

Safety precautions

Hazardous if not used properly, care should be taken when handling

InChI:InChI=1/C11H9NO/c1-8(13)11-7-12-6-9-4-2-3-5-10(9)11/h2-7H,1H3

Upstream product

• 58794-06-2 4-(1-hydroxyethyl)isoquinoline 
• 78593-42-7 4-ethynyl-4a,5-dihydroisoquinoline 
• 1532-97-4 4-bromoisoquinoline 
• 111-34-2 -butyl vinyl ether 
• 97674-02-7 tributyl(1-ethoxyvinyl)stannane 
• 194366-72-8 (1-ethoxyvinyl)zinc(II) chloride 
• 477723-66-3 4-(1-butoxy-vinyl)-isoquinoline 

Downstream Products

• 27301-96-8 1-isoquinolin-4-yl-1-phenyl-ethanol 
• 157834-78-1 2-benzyl-4-(1-N,N-dimethylaminoethyl)-1,2,3,4-tetrahydroisoquinoline 
• 157834-94-1 2-benzyl-4-<1-(N-formyl-N-methylamino)-ethyl>-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Palladium-catalyzed regiocontrolled internal heteroarylation of electron-rich olefins with heteroaryl halides

A highly efficient palladium-catalyzed Heck coupling reaction of heteroaryl halides with electron-rich vinyl ether and hydroxyalkyl vinyl ethers is described. It was found that the choice of solvent, ligand, and reaction temperature had a fundamental influence on the regioselectivity and reactivity of the reaction, and the combination of Pd(OAc)2 and DPPF in ethylene glycol led to the most effective catalytic system. Under these conditions, a variety of heteroaryl halides reacted very quickly with electron-rich olefins to afford exclusively the branched products in good to excellent yields without employing triflates, halide scavengers, or ionic liquids.

Syntheses of acetylquinolines and acetylisoquinolines via palladium-catalyzed coupling reactions

Acetylquinolines and acetylisoquinolines were obtained from the corresponding chloro-, bromo- or trifluoromethylsulfonyloxy-heteroaromatics via four different palladium-catalyzed coupling reactions: (i) Stille coupling with tri(n-butyl)-1-ethoxyvinylstannane; (ii) Negishi coupling with 1-ethoxyvinylzinc chloride; (iii) cross-coupling with tri(1-ethoxyvinyl)indium; (iv) Heck arylation of n-butyl vinyl ether.

Cyclising Nucleophilic Addition to Azinium Systems. Part 1. Reaction of 3-Indol-2-ylpyridine, 3-Indol-2-ylquinoline, 4-Indol-2-ylisoquinoline and Pyridocarbazoles with Acetic Anhydride

Two pyridocarbazoles were shown to react smoothly with acetic anhydride to give 1-acetyl-1,12a-dihydronaphthyridinocarbazol-11(12H)-ones. 3-Indol-2-ylquinoline and 3-indol-2-ylpyridine reacted in an analogous fashion though with further complications in the latter case. 4-Indol-2-ylisoquinoline gave E-2-acetyl-1-(1-acetylindol-2-ylmethylene)-2,3-dihydro-3-(2-oxopropyl)-1H-isoindole, the structure of which was determined by a detailed study of its (1)H n.m.r. spectrum with decoupling, n.O.e. and relaxation time measurements.