125455-89-2

Upstream product

• 125516-07-6 α-N-methyl-(+/-)-13α-hydroxyxylopinine p-toluenesulfonate 
• 60315-12-0 3-(2-vinyl-4,5-dimethoxyphenyl)-6,7-dimethoxy-1,2-dihydroisoquinol-1-one 
• 74-88-4 methyl iodide 
• 470461-18-8 (Z)-ethyl 1-(4,5-dimethoxy-2-vinylphenyl)-2-(3,4-dimethoxyphenyl)vinylcarbamate 
• 22185-86-0 ethyl 1-(3',4'-dimethoxybenzylidene)-3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinecarboxylate 
• 470461-20-2 [(Z)-2-(3,4-Dimethoxy-phenyl)-1-(4,5-dimethoxy-2-vinyl-phenyl)-vinyl]-methyl-carbamic acid ethyl ester 
• 136540-25-5 3-<2-(2-hydroxyethyl)-4,5-dimethoxyphenyl>-6,7-dimethoxy-2-methylisoquinolin-1-<2H>-one 
• 98-59-9 p-toluenesulfonyl chloride 
• 83527-65-5 (7R^*,13S^*,13aR^*)-(+/-)-7-methyl-13-hydroxy-2,3,10,11-tetramethoxydibenzoquinolizidinium iodide 

Downstream Products

• 199292-64-3 6,7-dimethoxy-3-[2-(2',2-dimethoxyethyl)-4,5-dimethoxyphenyl]-2-methyl-1(2H)-isoquinolinone 
• 136540-28-8 11-hydroxy-5,11-dimethyl-2,3,8,9-tetramethoxy-11H-indeno<1,2-c>isoquinolone 
• 140169-36-4 3-<2-(2-hydroxyethyl)-4,5-dimethoxyphenyl>-6,7-dimethoxy-2-methylisoquinolone O-acetate 
• 136540-26-6 O-methylfagaronine iodide 
• 15462-10-9 2,3,8,9-tetramethoxybenzophenanthridine 
• 125455-88-1 5,11-dimethyl-2,3,8,9-tetramethoxy-11H-indeno<1,2-c>isoquinolinium chloride 
• 136540-25-5 3-<2-(2-hydroxyethyl)-4,5-dimethoxyphenyl>-6,7-dimethoxy-2-methylisoquinolin-1-<2H>-one 
• 125455-90-5 5,11-dimethyl-2,3,8,9-tetramethoxy-11H-indeno<1,2-c>isoquinolone 
• 114253-63-3 O-methyl-6-oxofagaronine 

Relevant academic research and scientific papers

A new route to 3-(2-vinylphenyl)-2-methyl-2H-isoquinolin-1-ones and benzo[c]phenanthridines: Total synthesis of fagaronine

Treatment of N-carbethoxy-1-benzylideneisoquinolines with LDA gives N-ethoxycarbonyl-1-amino-1-(2-vinylphenyl)-2-phenylethylenes, which can be transformed into 3-(2-vinylphenyl)-2-methyl-2H-isoquinolin-1-ones by Bischler-Napieralski reactions, and thence

Applications of a novel carbon-nitrogen bond cleavage reaction: Part IV - A new biomimetic synthesis of benzo[c]phenanthridine alkaloids

A highly practical synthesis of benzo[c]phenanthridine alkaloids nitidine and 2-methoxyfagaronine has been developed from the corresponding protoberberines. The 8-oxoprotoberberines 1-3 on reaction with NaH and DMF give the C-N bond cleavage intermediates

BENZOPHENANTHRIDES. XV. SYNTHESIS OF O-METHYLFAGARONINE IODIDE AND CHLORIDE FROM 13α-HYDROXYXYLOPININE

Hydroborination of 3-(2-vinyl-4,5-dimethoxyphenyl)-6,7-dimethoxy-2-methyl-1,2-dihydro-1-isoquinolone gave 3--6,7-dimethoxy-2-methylisoquinolin-1-one, which was converted by the action of various oxidizing agents into a benzophenanthridone derivative. 5-Methyl-5,6-dihydro-2,3,8,9-tetramethoxybenzophenanthridine, obtained from the above benzophenanthridone by reduction with LiAlH4 in tetrahydrofuran at 0 deg C, was converted into O-methylfagaronine iodide by boiling in an ethanolic solution of I2 in the presence of Na acetate.On exchanging I- by Cl-, O-methylfagaronine chloride was obtained in a quantitative yield in boiling methanol with an excess of AgCl.

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

BENZOPHENANTHRIDINES. IX. SYNTHESIS OF 11-METHYL-C-NORFAGARONINE METHYL ETHER CHLORIDE FROM (+/-)-13α-HYDROXYXYLOPININE

The previously unknown chloride of 11-methyl-C-norfagaronine methyl ether was synthesized from (+/-)-13α-hydroxyxylopinine in four stages.A reduction in the number of stages in the biometic synthesis of the analog of benzophenanthridine alkaloids was achieved by the Hofmann degradation of α-N-methyl-(+/-)-13α-hydroxyxylopinine p-toluenesulfonate, accompanied by dehydration and oxidation.