- Extremely facile formation of the pavine alkaloid skeleton by the photoreaction between isoquinoline and benzyltrifluoroborate
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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
- Nishigaichi, Yutaka,Ohmuro, Yuuki,Hori, Yoshiki,Ohtani, Takuya
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supporting information
p. 118 - 120
(2020/02/25)
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- A new regioselective synthesis of isopavine and pavine alkaloids via double cyclization of N-(1,2-diarylethyl)-N-(2-phenylsulfinylethyl)formamide
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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.
- Shinohara, Tatsumi,Takeda, Akira,Toda, Jun,Sano, Takehiro
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p. 981 - 992
(2007/10/03)
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- Synthesis and reactions of N,N-bis[1-(trimethylsiloxy)alkyl]-formamides: Preparation of (±)-argemonine and (±)-norargemonine
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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.
- Johnson, A. Peter,Luke, Richard W. A.,Singh, Gurmaj,Boa, Andrew N.
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p. 907 - 913
(2007/10/03)
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- Evidence for a Radical Chain Mechanism for the Knabe Reaction of 1,2-Dihydro-2-methylpapaverine
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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.
- Langhals, Elke,Langhals, Heinz,Ruechardt, Christoph
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p. 1436 - 1454
(2007/10/02)
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