17656-61-0

Upstream product

• 21875-72-9 1-(4-methoxy-phenyl)-2-phenylsulfanyl-ethanone 
• 269-44-3 papraline 
• 123-11-5 4-methoxy-benzaldehyde 
• 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 
• 7099-91-4 p-methoxybenzoylformic acid 
• 40140-16-7 ethyl (p-methoxyphenyl)oxoacetate 
• 20341-14-4 N-[2-(1,3-benzodioxol-5-yl)ethyl]-2-(4-methoxyphenyl)acetamide 
• 471908-70-0 (4-methoxy-phenyl)-[6-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-methanone 
• 20341-46-2 (7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)(4-methoxyphenyl)methanone 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 13664-92-1 2,2-dibromo-1-(4-methoxyphenyl)ethanone 
• 402717-71-9 2-chloro-1-(4-methoxy-phenyl)-2-phenylsulfanyl-ethanone 

Downstream Products

• 20359-30-2 [1,3]dioxolo[4,5-g]isoquinolin-5-yl-(4-methoxy-phenyl)-methanol 

Relevant academic research and scientific papers

A facile biogenetic synthesis of pulcheotine A

Starting from homopiperonylamine and 4-methoxyphenylacetic acid, a facile biogenetic route to naturally occurring pulcheotine A has been demonstrated via Pictet-Spengler cyclization and two different air oxidation processes. Georg Thieme Verlag Stuttgart.

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.).

Transition metal-free Minisci reaction promoted by NCS, and TBHP: Acylation of heteroarenes

A method for acylation for heteroarenes under metal-free conditions has been described using NCS as an additive and TBHP as an oxidant. This method has been successfully employed in acylation of a variety of aldehyde with heteroarenes. The application of the method has been illustrated in synthesizing isoquinoline derived natural products. This strategy provides an efficient, mild and inexpensive method for acylation of heteroarenes.

Synthesis of isoquinoline alkaloids via oxidative amidation-bischler- napieralski reaction

A straightforward synthesis of -keto amides by coupling primary amines with aryl dibromoethanones under oxidative amidation conditions has been developed. The -keto amides were then subjected to heterocyclodehydration reaction under Bischler-Napieralski conditions followed by aromatization with DBU provided 1-benzoyl isoquinolines in a two-stage process. Utilizing this methodology, isoquinoline alkaloids such as thalmicrinone, papavaraldine, and pulcheotine A were synthesized in excellent yields. Georg Thieme Verlag Stuttgart · New York.

Desulfonylation of N-sulfonyl tetrahydroisoquinoline derivatives by potassium fluoride on alumina under microwave irradiation: Selective synthesis of 3,4-dihydroisoquinolines and isoquinolines

In a solvent-free system, the microwave irradiation of mixtures of N-sulfonyl tetrahydroisoquinolines and 37% potassium fluoride supported on alumina selectively furnished 3,4-dihydroisoquinolines or isoquinolines, depending upon the reaction time.

Elaboration of 1-benzoyltetrahydroisoquinoline derivatives employing a Pictet-Spengler cyclization with α-chloro-α-phenylthioketones. Synthesis of O-methylvelucryptine

The reaction of N-tosyl-β-phenethylamines with α-chloro-α-phenylthioketones, leading to 1-benzoyl- and 1-pivaloyl-tetrahydroisoquinolines under modified Pictet-Spengler conditions, is described. The synthesis of O-methylvelucryptine employing this transformation as a key step is reported.