- Synthesis of cyclic imines via ethylenetetramethyldisilyl-protected ω-aminoimines. Application to the synthesis of alkaloids
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Cyclic imines, including several alkaloids such as myosmine, anabaseine and apoferrorosamine, were synthesized by α-alkylation of imines with ethylenetetramethyldisilyl-protected ω-bromoamines, followed by ring closure.
- De Kimpe, Norbert G.,Kepppens, Marian A.,Stevens, Christian V.
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- Method for synthesis of 4-OH substituted anabaseine derivative
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A method for synthesis of 4-OH substituted anabaseine derivative which is used as an α7 receptor agonist is revealed. A nucleophilic substitution reaction of δ-valerolactam with ethyl nicotinate is carried out to get an intermediate product. Th
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Page/Page column 3; 5; 6
(2017/03/08)
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- The reaction of cyclic imines with the Ruppert-Prakash reagent. Facile approach to α-trifluoromethylated nornicotine, anabazine, and homoanabazine
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We have demonstrated that the Ruppert-Prakash reagent is able to react with a number of cyclic imines under acidic condition to afford the corresponding α-trifluoromethyl derivatives of nitrogen heterocycles. 5-7-Membered cyclic imines bearing various alkyl, aryl or heterocyclic group were successfully involved in this transformation. Novel trifluoromethylated analogues of nicotine, anabasine, and homoanabasine alkaloids were synthesized.
- Shevchenko, Nikolay E.,Vlasov, Katja,Nenajdenko, Valentine G.,R?schenthaler, Gerd-Volker
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scheme or table
p. 69 - 74
(2011/02/27)
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- Organometallic Ring-Opening Reactions of N-Acyl and N-Alkoxycarbonyl Lactams. Synthesis of Cyclic Imines
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The reactions of hexyl- and phenylmagnesium bromides with N-acyl and N-alkoxycarbonyl lactams in tetrahydrofuran at -78 deg C have been performed to determine the factors affecting the regioselectivity.N-Pivaloyl γ- and δ-lactams undergo the ring-opening reactions with both Grignard reagents, whereas on the N-benzoyl γ-lactam a complete selectivity is achieved only with phenylmagnesium bromide.The N-Cbz γ- and δ-lactams preferentially react at the exocyclic carbonyl group, especially with hexylmagnesium bromide.The N-Boc five- to eight-membered lactams undergo the ring-opening reaction to give N-Boc-ω-amino ketones, although the efficiency slightly decreases by increasing the ring size.The deprotection of the N-Boc-ω-amino ketones with trifluoroacetic acid easily affords the corresponding five- to seven-membered cyclic imines.Pyridine alkaloids containing the cyclic imine moiety have been prepared by a modified route, exploiting the more easily available pyridyllithium reagents, instead of the corresponding Grignard reagents.
- Giovannini, Arianna,Savoia, Diego,Umani-Ronchi, Achille
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p. 228 - 234
(2007/10/02)
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- SYNTHESIS OF TOBACCO ALKALOIDS VIA TERTIARY AZIDES
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A convenient new synthesis of different tobacco alkaloids, such as nicotine and anabasine is described, using as key step the SCHMIDT reaction applied to tertiary alcohols.
- Alberici, Gilles F.,Andrieux, Jean,Adam, Gerard,Plat, Michel M.
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p. 1937 - 1940
(2007/10/02)
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