20345-67-9

Upstream product

• 112970-38-4 2-acetyl-1-(4-chlorobenzylidene)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline 
• 47216-54-6 1-(4-chloro-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 1878-66-6 4-chlorophenylacetic Acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 25026-34-0 4-chlorophenacetyl chloride 
• 10268-55-0 N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-chlorophenyl)-acetamide 

Downstream Products

• 20359-08-4 (4-chlorophenyl)(6,7-dimethoxyisoquinolin-1-yl)methanone 

Relevant academic research and scientific papers

Copper(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to 3,4-dihydroisoquinolines using air (O2) as a clean oxidant

A mild, efficient and eco-friendly method for the oxidation of 1-Bn-DHIQs to 1-Bz-DHIQs without concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs is very important for the syntheses of 1-Bz-DHIQ alkaloids and analogues. In this article, we developed a novel Cu(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to the C-1 positions of various 1-Bn-DHIQs. It was observed that when 0.2 equiv. of Cu(OAc)2·2H2O was used as the catalyst, 3.0 equiv. of AcOH was used as the additive and air (O2) was used as a clean oxidant, various 1-Bn-DHIQs could be efficiently oxidized to corresponding 1-Bz-DHIQs at 25 °C in DMSO. Especially, almost no concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs was observed during the above reaction. In addition, this method was successfully applied in the first total synthesis of the alkaloid canelillinoxine.

A facile synthesis of 1-oxo-pyrrolo[2,1-a]isoquinolines

The facile synthesis of 1-oxo-pyrrolo[2,1-a]isoquinolines from the reaction of 1-aroyl-3,4-dihydroisoquinolines and symmetrical alkynes in toluene is described. The novel compounds contain functional groups that are suitable for further modification.

Domino Reactions of 1-Aroyl-3,4-dihydroisoquinolines with α,β-Unsaturated Aldehydes

An efficient synthesis of pyrrolo[2,1- a ]isoquinolines by a domino reaction from a variety of 3,4-dihydropyrrolo[2,1- a ]isoquinolines and α,β-unsaturated aldehydes in the absence of catalyst in good yields under microwave irradiation, is reported.

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.

Synthesis of 6,7-dimethoxy-1-halobenzyl-1,2,3,4-tetrahydroisoquinolines

Some 6,7-dimethoxy-1-halobenzyl-1,2,3,4-tetrahydroisoquinolines were synthesized from 2-(3,4-dimethoxyphenyl)ethylamine and halophenylacetic acids in three steps in good yield.

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.