54879-37-7

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 54879-80-0 (3,5-Dimethoxy-benzyl)-(2,2-dimethoxy-ethyl)-amine 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 58754-95-3 N-(2,2-dimethoxyethyl)-p-toluenesulfonamide 

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.

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.