79082-64-7

Usage

InChI:InChI=1/C21H21NO6/c1-22-7-6-11-8-15(24-2)16(25-3)9-13(11)18(22)19-12-4-5-14-20(27-10-26-14)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18-,19+/m1/s1

Upstream product

• 485-51-8 (+/-)-corlumine 
• 21414-43-7 l-adlumidine 
• 524-46-9 (+)-adlumine 
• 64361-55-3 6-((E)-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-isoquinolin-1-ylidene)-6H-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-8-one 
• 30045-07-9 2-methyl-6,7-dimethoxy-3,4-dihydroisoquinolinium iodide 
• 125239-01-2 Potassium; 8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxole-6-carboxylate 
• 80053-50-5 6,7-methylenedioxy-3-chlorophthalide 
• 201230-82-2 carbon monoxide 
• 58343-48-9 5-formyl-benzo[1,3]dioxole-4-carboxylic acid 
• 124-38-9 carbon dioxide 
• 56008-63-0 4-bromobenzo[d][1,3]dioxole-5-carbaldehyde 
• 64395-09-1 8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxole-6-carboxylic acid (3,4-dimethoxy-phenethyl)-methyl-amide 
• 247579-61-9 1-[2-bromo-3,4-(methylenedioxy)benzoyl]-6,7-dimethoxy-3,4-dihydroisoquinoline 
• 247579-54-0 N-(3,4-dimethoxyphenethyl)-2-bromo-3,4-(methylenedioxy)phenylacetamide 

Downstream Products

• 485-51-8 (+)-corlumine 

Relevant academic research and scientific papers

Synthesis of phthalideisoquinoline and protoberberine alkaloids and indolo[2,1-α]isoquinolines in a divergent route involving palladium(0)- catalyzed carbonylation

6,7,3',4'-Alkoxy-substituted 1-(2'-bromobenzoyl)-3,4-dihydroisoquinoline methiodides 17 were treated with sodium borohydride in methanol or acetic acid to give erythro-1-(2'-bromo-α-hydroxybenzyl)-2-methyl-1,2,3,4- tetrahydroisoquinolines 19. Treatment of 17 with lithium aluminum hydride in tetrahydrofuran gave the threo-isomer 20 in preference to the erythro 19. On the basis of studies on palladium(0)-catalyzed carbonylation of 2-bromo-3,4- dimethoxybenzyl alcohol to 6,7-dimethoxyphthalide, amino alcohol 19 or 20 was treated with a catalytic amount of palladium(II) acetate and triphenylphosphine in an atmosphere of carbon monoxide in the presence of chlorotrimethylsilane and potassium carbonate in boiling toluene to give the corresponding erythro- or threo-types of phthalideisoquinoline alkaloids 1 or 2, respectively. One-pot cyclization of the erythro-amino alcohols 19 was achieved by heating in N,N-dimethylformamide containing potassium carbonate to give 2,3,8,9- or 2,3,9,10-alkoxy-substituted 5,6-dihydroindolo[2,1- α]isoquinolines 3, which have a unique tetracyclic skeleton characteristic of dibenzopyrrocoline alkaloids. Similarly, palladium-(0)-catalyzed carbonylation of 1-(2'-bromobenzyl)tetrahydroisoquinolines 21 in the presence of excess potassium carbonate was found to give 8-oxoberbines 22, which on reduction with lithium aluminum hydride can be converted to protoberberine alkaloids 4.

Studies on Carboxylation of Alkoxy-Substituted Benzyl Alcohols via Direct Lithiation and Bromine-Lithium Exchange: Synthesis of Phthalides and Phthalideisoquinoline Alkaloids

Conversion of alkoxy-substituted benzyl alcohols to the corresponding phthalides by carboxylation via ortho lithiation and bromine-lithium exchange was studied.The method was applied to the key step in the synthesis of phthalideisoquinoline alkaloids.

A FACILE SYNTHESIS OF PHTHALIDEISOQUINOLINES BY DECARBOXYLATION OF PHTHALIDECARBOXYLATES IN THE PRESENCE OF IMINE METHIODIDES

Decarboxylation of potassium phthalide-3-carboxylates in the presence of acyclic imine methiodides in DMSO leads mainly to 2-acylbenzamides, but with 3,4-dihydroisoquinolinium methiodides, a one step synthesis of phthalideisoquinolines is achieved in mode

Synthesis of phthalideisoquinolines from 3-halophthalides and 3,4-dihydroisoquinolinium salts

Phthalideisoquinoline alkaloids have been synthesized by coupling appropriately substituted 3-halophthalides and 2-methyl-3,4-dihydroisoquinolinium salts in the presence of Zn(Cu) couple or metallic Zn.Both erythro and threo isomers are formed in the reaction.The nmr spectra of the (+/-)-erythro- and (+/-)-threo-isocordrastines have been reinvestigated.The results, which differ from those previously reported, lead to a different conclusion regarding the conformations of the molecules.