39964-90-4

Upstream product

• 495-76-1 piperonol 
• 120-57-0 piperonal 
• 54879-81-1 (2H-1,3-benzodioxol-5-ylmethyl)(2,2-dimethoxyethyl)amine 
• 98-59-9 p-toluenesulfonyl chloride 
• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 58754-95-3 N-(2,2-dimethoxyethyl)-p-toluenesulfonamide 

Downstream Products

• 87489-85-8 (2-bromophenyl)([1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanone 
• 475-75-2 liriodenine 
• 17656-61-0 (6,7-methylenedioxyisoquinolinyl)-(4'-methoxyphenyl)-methanone 
• 64880-96-2 6-tosyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 39964-98-2 2-benzoyl-6,7-methylenedioxy-1,2-dihydroisoquinoline-1-carbonitrile 
• 123796-55-4 O-benzylberbithine 
• 105798-91-2 berbithine 
• 70400-40-7 1-(3-hydroxy-4-methoxybenzyl)-6,7-methylenedioxyisoquinoline 
• 38750-43-5 O-benzylisosevanine 
• 54879-55-9 6-(toluene-4-sulfonyl)-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinoline 

Relevant academic research and scientific papers

Synthesis of tetrahydroisoquinolines through TiCl4-mediated cyclization and Et3SiH reduction

A versatile and efficient telescoped reaction sequence for the synthesis of tetrahydroisoquinolines (THIQs) is reported that uses TiCl4 to promote cyclization of a benzylaminoacetal derivative and Et3SiH for reduction of the intermediate 4-hydroxy-THIQ. This method is complimentary to the classical Pomeranz-Fritsch and related reactions since it tolerates electron-withdrawing substituents and allows access to 8-substituted THIQs.

Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions

Isoquinolines activated with sulfamoyl chlorides were reacted with indoles in a 3-component reaction to generate a library of dihydroisoquinoline derivatives. Using a differential protecting group strategy, products could be further derivatised. Synthesis of isoquinoline starting materials using several different methods is also described.

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.).

A SIMPLIFIED ISOQUINOLINE SYNTHESIS

A simple variation of the Pomeranz-Fritsch cyclization provides a short, efficient route to isoquinolines.Treatment of benzylic halides or mesylates 1 with the sodium anion of N-tosyl aminoacetaldehyde dimethyl acetal (2) followed by acid-catalyzed cyclization provides an effective, two-step preparation of isoquinolines 4.