20345-69-1

Upstream product

• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 
• 91790-53-3 1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4-dimethoxybenzyl)isoquinoline 
• 6957-27-3 3,4-dihydropapaverine 
• 86119-84-8 phosphoric acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 10313-60-7 3,4-dimethoxyphenylacetyl chloride 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 50896-90-7 (-) N-norlaudanosine 
• 1236909-15-1 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)-2-oxoacetamide 
• 123796-71-4 3-(3,4-Dimethoxy-phenyl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid tert-butyl ester 
• 13074-31-2 Tetrahydropapaverine 
• 61348-95-6 (Z)-1-<(3,4-Dimethoxyphenyl)methylene>-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 72527-19-6 2-(3,4-dimethoxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]thioacetamide 

Downstream Products

• 137465-62-4 2-benzoyl-1-cyano-6,7-dimethoxy-1-(3',4'-dimethoxybenzoyl)-1,2,3,4-tetrahydroisoquinoline 
• 62926-27-6 (6,7-dimethoxy-3,4-dihydro-isoquinolin-1-yl)-(3-hydroxy-4-methoxy-phenyl)-methanone 
• 83177-81-5 (7-Hydroxy-6-methoxy-3,4-dihydro-isoquinolin-1-yl)-(3-hydroxy-4-methoxy-phenyl)-methanone 
• 83177-80-4 (3,4-Dimethoxy-phenyl)-(7-hydroxy-6-methoxy-3,4-dihydro-isoquinolin-1-yl)-methanone 
• 62926-29-8 erythro-(+/-)-α-hydroxynorlaudanosine 
• 62926-29-8 erythro (+/-)-α-hydroxylaudanosine 
• 522-57-6 papaveraldine 
• 13074-31-2 Tetrahydropapaverine 

Relevant academic research and scientific papers

Self-Sensitized Photo-Oxidation of 1-Benzyl-3,4-dihydroisoquinolines

The air oxidation of 1-benzyl-3,4-dihydroisoquinolines is shown to be a self-sensitized photo-oxidation proceeding via singlet oxygen.

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.

One-Pot Synthesis of Papaverine Hydrochloride and Identification of Impurities

Abstract: A one-pot synthesis of papaverine hydrochloride with 99.6% purity was performed using xylene as solvent for the entire process. The critical parameters of each step, as well as the impurities generated, were identified. The overall yield was improved to 63%. The proposed synthetic procedure is suitable for industrial production.

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.

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.

Efficient and Practical Syntheses of Enantiomerically Pure (S)-(-)-Norcryptostyline I, (S)-(-)-Norcryptostyline II, (R)-(+)-Salsolidine and (S)-(-)-Norlaudanosine via a Resolution-Racemization Method

Four racemic tetrahydroisoquinolines (RS)-(±)-1-4 were prepared from homoveratrylamine via amidation, Bischler-Napieralski reaction and the subsequent reduction. The enantiomerically pure tetrahydroisoquinolines (S)- (-)-norcryptostyline I [(S)-(-)-1], (S)-(-)-norcryptostyline II [(S)-(-)-2], (R)-(+)-salsolidine [(R)-(+)-3] and (S)-(-)-norlaudanosine [(S)-(-)-4] were then obtained in 45%, 40%, 41% and 38% yields, respectively, via resolution of the racemic compounds (RS)-(±)-1-4 with half equivalent of chiral acids. In addition, the enantiomerically enriched compounds (R)-(+)-1, (R)-(+)-2, (S)-(-)-3 and (R)-(+)-4 from the mother liquors were efficiently racemized via a one-pot redox method in almost quantitative yields.

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.

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.

THE CHEMISTRY OF VICINAL TRICARBONYL COMPOUNDS. APPLICATIONS IN THE SYNTHESIS OF ISOQUINOLINE ALKALOIDS

The central carbonyl of a vicinal tricarbonyl system is used as a dielectrophile with substituted phenethylamines in short, efficient syntheses of the isoquinoline alkaloids, papaveraldine, hydrastine and cordrastine.

BENZOPHENANTHRIDINES. VI. TRANSFORMATIONS OF PROTOBERBERINE ALKALOIDS INTO BENZOPHENANTHRIDINE ALKALOIDS. HOFMANN DEGRADATION OF α-N- AND β-N-METHYL-(+/-)-13α-HYDROXYXYLOPININE IODIDES

(+/-)-13α-Hydroxyxylopinine was synthesized from 3,4-dihydropapaverine dichlorophosphate through a stage involving the formation of 3,4-dihydropapaveraldine and α-hydroxynorlaudanosine.The product was converted by the action of methyl iodide in ethanol in