5531-95-3

Usage

Uses

(-)-Argemonine is a pavine alkaloid that has shown some cytotoxic and anti-HIV activity.

InChI:InChI=1/C21H25NO4/c1-22-16-6-12-8-18(23-2)20(25-4)10-14(12)17(22)7-13-9-19(24-3)21(26-5)11-15(13)16/h8-11,16-17H,6-7H2,1-5H3

Upstream product

• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 2246-26-6 1,2-dihydro-2-methylpapaverine 
• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 
• 177963-88-1 N,N-Bis-[2-(3,4-dimethoxy-phenyl)-1-trimethylsilanyloxy-ethyl]-formamide 
• 5703-21-9 3,4-dimethoxyphenylacetaldehyde 

Downstream Products

• 17482-72-3 4',5',4'',5''-Tetramethoxy-7-benzylmethyl-amino-dibenzo<1.2,5.6>cyclooctatrien-(1,3,5) 
• 17482-72-3 (+/-)-N-Benzyl-pavinmethin 

Relevant academic research and scientific papers

Extremely facile formation of the pavine alkaloid skeleton by the photoreaction between isoquinoline and benzyltrifluoroborate

Appling the photo-benzylation of isoquinoline with benzyltrifluoroborate, an extremely facile method for the construction of a pavine alkaloid skeleton was developed. When 3-methoxybenzylboron reagents were employed to the reaction, it was found that not

A new regioselective synthesis of isopavine and pavine alkaloids via double cyclization of N-(1,2-diarylethyl)-N-(2-phenylsulfinylethyl)formamide

Pummerer reaction of N-[1,2-(3,4-dimethoxyphenyl)ethyl]-N-(2-phenylsulfinylethyl)formamide (9) using trifluoroacetic anhydride and boron trifluoride etherate caused double cyclization to give N-formylisopavine (21). Acid catalyzed cyclization of the 1,2-dihydroisoquinoline (23) prepared from 4-phenylthio-1,2,3,4-tetrahydroisoquinoline (11) gave N-formylpavine (26). LiAlH4 reduction of the N-formates (21 and 26) gave (±)-O-methylthalisopavine (4) and (±)-argemonine (5), respectively.

Synthesis and reactions of N,N-bis[1-(trimethylsiloxy)alkyl]-formamides: Preparation of (±)-argemonine and (±)-norargemonine

Symmetrical and unsymmetrical N,N-bis[1-(trimethylsiloxy)alkyl]formamides are prepared and their reactions investigated, including an application to the synthesis of the pavine alkaloids (±)-argemonine and (±)-norargemonine.

Evidence for a Radical Chain Mechanism for the Knabe Reaction of 1,2-Dihydro-2-methylpapaverine

A free radical chain mechanism is proposed for the Knabe reaction and the accompanying elimination reaction on account of their nonintegral reaction order and of successful inhibition experiments. 3,4-Dimethoxybenzyl radicals are the chain carrying species.Battersby's synthesis of N-methylpavine (19) from 1,2-dihydro-2-methylpapaverine (9) is dependent on the presence of formic acid as radical chain inhibitor.In the presence of inhibitors 1-benzyl-1,4-dihydro-2-methylisoquinolinium ions like 10 are persistent species whose chemistry can now be investigated.