1383571-57-0

Upstream product

• 1532-72-5 isoquinoline N-oxide 
• 65185-68-4 o-bromonitrostyrene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 119-65-3 isoquinoline 
• 2142-69-0 2-bromophenyl methyl ketone 
• 26767-16-8 2-(2-bromophenyl)-2-oxoacetic acid 
• 101439-09-2 (2-bromophenyl)isoquinolin-1-yl-acetonitrile 
• 491-30-5 1-isoquinolone 
• 19658-77-6 1-iodoisoquiniline 
• 7154-66-7 2-bromobenzoic acid chloride 

Downstream Products

• 38750-39-9 7H-dibenzo[de,g]quinolin-7-one 
• 78792-59-3 (2-bromophenyl)(isoquinolin-1-yl)methanol 

Relevant academic research and scientific papers

Minisci aroylation of N-heterocycles using choline persulfate in water under mild conditions

Metal persulfate mediated thermal oxidative organic transformations invariably require a higher temperature and frequently use an organic solvent. The objective of this work was to develop persulfate mediated oxidative transformations that can be performed nearly at room temperature using water as a solvent. This report describes modified Minisci aroylation of isoquinolines with arylglyoxylic acids using choline persulfate and its pre-composition (choline acetate and K2S2O8) in water at 40 °C. A few other nitrogen heterocycles were also utilized affording various aroylated products in good to excellent yields. Unlike metal persulfate that could produce metal salt byproducts, a key feature of the chemistry reported herein includes the use of environmentally benign choline persulfate containing biodegradable choline as a counter-cation, the Minisci reaction demonstrated at 40 °C in water as the only solvent, and unconventional activation of persulfate. This journal is

Visible-Light-Triggered, Metal- and Photocatalyst-Free Acylation of N-Heterocycles

A photoinduced acylation of N-heterocycles is explored. This visible-light triggered reaction occurs not only under extremely mild reaction conditions, but also does not require the presence of a photosensitizer. The mechanistic studies suggest formation of EDA complexes prompt to harness the energy from visible-light. Compatibility with a large panel of α-keto acids as acyl precursors and an array of N-heterocycles clearly showcase the synthetic potential of this handy and green acylation protocol. (Figure presented.).

Palladium(II)-catalyzed C-C and C-O bond formation for the synthesis of C1-benzoyl isoquinolines from isoquinoline: N -oxides and nitroalkenes

C1-Benzoyl isoquinolines can be generated via a palladium(ii)-catalyzed C-C and C-O coupling of isoquinoline N-oxides with aromatic nitroalkenes. The reaction proceeds through remote C-H bond activation and subsequent intramolecular oxygen atom transfer (OAT). In this reaction, the N-O bond was designed as a directing group in the C-H bond activation as well as the source of an oxygen atom.

Direct conversion of 1-(2-bromobenzoyl)isoquinolines to dibenzo[ de,g ]quinolin-7-ones via reductive photocyclization

A series of A/D-ring substituted dibenzo[de,g]quinolin-7-ones was produced from the corresponding isoquinolinones and (2-bromophenyl)acetonitriles in four steps. This represents a convenient approach toward the synthesis of tetracyclic alkaloids. A direct conversion of 1-(2-bromobenzoyl)isoquinolines to dibenzo[de,g]quinolin-7-ones is the key step in the total synthesis. The yield of the reductive photocyclization depends on the position of the substituents at the isoquinolyl ring and the phenyl group. The mechanism of the reductive photocyclization is also discussed.

METALLIC AMIDOBORATES FOR FUNCTIONALIZING ORGANIC COMPOUNDS

Metallic amidoborates, their anions and processing for making them are described which comprise at least one metallic cation or cationic complex and an anion comprising the moiety (R1)2N -B(R2)3, wherein each R1 independently represents Z1(Z1A)p-, wherein each Z1 and Z1A independently represents a carbon atom or a silicon atom and each p independently represents the integer 2 or 3 and each R2 independently represents a fluorine atom or Z2(Z2A)k -, wherein each Z2 independently represents a carbon atom, nitrogen atom or a silicon atom, each Z2A independently represents a hydrogen atom, a carbon atom or a silicon atom, and k represents a positive integer equal to the valence of Z2, wherein at least one of the R2 substituents is Z2(Z2A)k -. The metallic amidoborate compounds may be used to make metalated organic compounds, which in turn may be reacted with an electrophile to make organic compounds functionalized by the electrophile residue. The metallic amidoborate bases described herein are exceptionally stable, so that functionalization of the organic compound may be carried out rapidly and with high yield at room temperature.