87489-85-8

Upstream product

• 76525-21-8 (2-bromophenyl)(7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanone 
• 39964-90-4 N-(2,2-dimethoxyethyl)-N-<(3,4-methylenedioxyphenyl)methyl>-p-toluenesulfonamide 
• 54879-81-1 (2H-1,3-benzodioxol-5-ylmethyl)(2,2-dimethoxyethyl)amine 
• 120-57-0 piperonal 
• 2142-69-0 2-bromophenyl methyl ketone 
• 269-44-3 papraline 
• 26767-16-8 2-(2-bromophenyl)-2-oxoacetic acid 
• 24188-76-9 [1,3]dioxolo[4,5-g]isoquinolin-5(6H)-one 
• 1432725-49-9 1-iodo-6,7-(methylenedioxy)isoquinoline 
• 1432725-70-6 (2-bromophenyl)(6,7-methylenedioxyisoquinolin-1-yl)acetonitrile 
• 87201-30-7 N-<-2-(3,4-methylenedioxyphenyl)ethyl>-2'-bromophenylacetamide 
• 87201-31-8 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 18698-97-0 ortho-bromophenylacetic acid 

Downstream Products

• 475-75-2 liriodenine 
• 87489-86-9 1-(2'-bromo-α-hydroxybenzyl)-6,7-methylenedioxyisoquinoline 

Relevant academic research and scientific papers

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.).

Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.

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.

Synthetic Photochemistry: Synthesis of Liriodenine

Bischler-Napieralski cyclisation of N--2'-bromophenylacetamide (3) followed by manganese dioxide oxidation of the crude amine (4) gives 1-(2'-bromobenzoyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline (5) which is aromatis