20359-08-4

Upstream product

• 47216-54-6 1-(4-chloro-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 47216-53-5 1-(4-chlorobenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 20345-67-9 (4-chlorophenyl)(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methanone 
• 112970-38-4 2-acetyl-1-(4-chlorobenzylidene)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline 

Downstream Products

• 47216-53-5 1-(4-chlorobenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Oxidation of 1-benzyldihydroisoquinolines or 1- benzyltetrahydroisoquinolines with dioxygen to 1-benzoylisoquinolines

An environmental-benign methodology to synthesize 1-benzoylisoquinolines from 1-benzyl-3, 4-dihydroisoquinolines or 1-benzyl-1,2,3,4- tetrahydroisoquinolines using dioxygen as an oxidant was developed. This methodology in combination with Bischler-Napieralski reaction leads to a facile synthesis of 1-benzoylisoquinolines from phenylacetic acids and phenylethanamines.

Strategies and synthetic methods directed toward the preparation of libraries of substituted isoquinolines

Strategies for the production of substituted isoquinoline libraries were developed and explored. Routes involving microwave-assisted variants of the Bischler-Napieralski or Pictet-Spengler reaction allowed for cyclization of substituted β-arylethylamine derivatives. The dihydroisoquinolines and tetrahydroisoquinolines thus generated could then be oxidized to their corresponding isoquinoline analogues. An alternate strategy, however, involving the preparation and activation of isoquinolin-1(2H)-ones is demonstrated to be a more practical, rapid, and efficient route to C1- and C4-substituted isoquinoline libraries.

Antiplatelet activity of benzylisoquinoline derivatives oxidized by cerium(IV) ammonium nitrate

Oxidation of 1-benzyl-3,4-dihydroisoquinolines with cerium(IV) ammonium nitrate (CAN) under mild condition yielded the mixture of corresponding 1-benzylisoquinolines (b-type) and 1-benzoylisoquinolines (a- or c-type) in an equal yields. The selective oxidation products (c-type) can be prepared by using MeCN instead of MeOH. In the antiplatelet assays, four inducers were employed, including AA, Col, PAF, and Thr. In the PAF or Col induced platelet aggregation, compounds belonging to a- and b-type showed stronger inhibitory effects than aspirin.

Lead Tetraacetate Mediated Oxidation of the Enamides Derived from 1-Benzyl-3,4-dihydroisoquinolines

The products obtained from the lead tetraacetate (LTA) oxidation of N-acylbenzylidene isoquinoline enamides are a function of the type of carbonyl function in the enamide, the solvent,and the type of substitution on the benzylidene aromatic ring.The benzoyl enamides yield Z-β-acethoxy-substituted enamides.The ethoxycarbonyl enamides, containing electron-releasing substituents on the benzylidene ring, efficiently form oxazolones when oxidized with LTA in acetic acid.In the absence of electron-releasing substituents, ring opening occurs to form benzoin esters.When the same oxidation is conducted in benzene, the enamide double bond is converted into its diacetoxy derivative, which can undergo a variety of reactions.LTA oxidation of acetyl enamides results in cleavage of the acetyl group with ultimate formation of 1-benzoyl-3,4-dihydroisoquinolines and isoquinolines.Oxidation of the formyl enamide with LTA results in cleavage of the formyl group with formation of a variety of products.Most of these have an acetyl group in place of the original formyl and are the result of either cleavage of the benzylidene ring at the double bond, oxidation, and subsequent ring opening to a benzil or various other oxidative and rearrangement processes.

Rearrangement of 1-(α-Hydroxybenzyl)-1,2,3,4-tetrahydroisoquinolines to 1-Phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines

When methoxy-substituted 1-(α-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinolines are heated in formic acid they rearrange initially to give 5-phenyl-2,3-dihydro-1H-3-benzazepines which, on further heating in formic acid, are reduced to 1-phenyl-2,3,4,5-tetrah