19918-74-2

Upstream product

• 2221-44-5 5-(3,4-dimethoxy-benzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 20341-16-6 N-(2-benzo[1,3]dioxol-5-yl-ethyl)-2-(3,4-dimethoxy-phenyl)-acetamide 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 

Downstream Products

• 6656-19-5 (+-)-2,3-methylenedioxy-10,11-dimethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine 
• 81165-49-3 3-[5-(3,4-Dimethoxy-benzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]-propionic acid 2-{3-[5-(3,4-dimethoxy-benzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]-propionyloxy}-ethyl ester; compound with oxalic acid 
• 81165-50-6 3-[5-(3,4-Dimethoxy-benzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]-propionic acid 5-{3-[5-(3,4-dimethoxy-benzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]-propionyloxy}-pentyl ester; compound with oxalic acid 
• 64229-26-1 C₄₈H₅₈N₂O₁₂⁽²⁺⁾*2I^(1-) 
• 64229-27-2 C₅₁H₆₄N₂O₁₂⁽²⁺⁾*2I^(1-) 
• 5544-50-3 5-(3,4-dimethoxybenzyl)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline 

Relevant academic research and scientific papers

Identification of N-benzyltetrahydroisoquinolines as novel anti-neuroinflammatory agents

A series of simplified berberine analogs was designed, synthesized, and evaluated for anti-inflammatory activity. SAR studies identified N-benzyltetrahydroisoquinoline 7d as a potent berberine analog. 7d suppressed LPS-induced inflammatory cytokine levels

Synthesis of 8-oxoberbines and related benzolactams by Pd(OAc) 2-catalyzed direct aromatic carbonylation

A variety of alkoxy-substituted benzolactams with a berbine or yohimbane skeleton were prepared from 1-benzyl-1,2,3,4-tetrahydroisoquinolines or 1-benzyl-1,2,3,4-tetrahydro-β-carbolines by a phosphine-free Pd(II)-catalyzed direct aromatic carbonylation in a Pd(OAc)2-Cu(OAc) 2 catalytic system. The site selectivity was compared with that of the carbonylation with Pd(OAc)2 or Pd(OAc)2·2 PPh3, respectively.

Synthesis of (±)-Glaucine and (±)-Neospirodienone via an One-Pot Bischler-Napieralski Reaction and Oxidative Coupling by a Hypervalent Iodine Reagent

Condensation of 3,4-dimethoxybenzeneethanamine (3d) and various benzeneacetic acids, i.e., 4a-e, via a practical and efficient one-pot Bischler-Napieralski reaction, followed by NaBH4 reduction, produced a series of 1-benzyl-1,2,3,4-tetrahydroisoquinolines, i.e., 5a-e, in satisfactory yields (Scheme 3). Oxidative coupling of the N-acyl and N-methyl derivatives 6a-e of the latter with hypervalent iodine ([IPh(CF 3COO)2]) yielded products with two different skeletons (Scheme 4). The major products from N-acyl derivatives 6a-c were (±)-N-acylneospirodienones 2a-c, while the minor was the 3,4-dihydroisoquinoline 7. (±)-Glaucine (1), however, was the major product starting from N-methyl derivative 6e. Possible reaction mechanisms for the formation of these two types of skeleton are proposed (Scheme 5).