- Organic Superbase t-Bu-P4 Catalyzes Amination of Methoxy(hetero)arenes
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We report that the organic superbase t-Bu-P4 efficiently catalyzes the amination of methoxy(hetero)arenes with amine nucleophiles such as aniline, indoline, and aminopyridine derivatives. This catalytic reaction is effective for the transformation of elec
- Shigeno, Masanori,Hayashi, Kazutoshi,Nozawa-Kumada, Kanako,Kondo, Yoshinori
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supporting information
p. 5505 - 5508
(2019/08/01)
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- On the thermally induced rearrangement of 2-alkoxypyridines to N-alkylpyridones
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Analogues of 2-methoxypyridine undergo rearrangement to N-methylpyridones under flash vacuum pyrolysis (FVP) conditions. Ethoxy derivatives undergo competitive ethyl migration and elimination of ethylene. Analogues of 4-methoxypyridine do not undergo rearrangement under FVP conditions, but demethylation on silica may occur. The ease of rearrangement follows the basicity of the alkoxyhetarene to some extent. The vapour-phase rearrangements have been contrasted to condensed-phase pyrolyses. and a four-centre transition state for the former is supported by computation. The rearrangement allows structural assignment to the two products from the reaction of 2,4-dichloroquinoline with pyrrolidine.
- Lister, Troy,Prager, Rolf H.,Tsaconas, Michael,Wilkinson, Kerry L.
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p. 913 - 916
(2007/10/03)
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- Heterocyclic Seven-Membered Ring Compounds, XXXIII. - Synthesis and Properties of 5-Methoxy-1,4-benzothiazepine and of 5-Methoxy-1-methyl-1,4-benzothiazepinium Tetrafluoroborate
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Acid-catalyzed cyclisation of the amide acetal 2 yields the seven-membered ring lactam 3 which could be N-methylated to give compound 4 by treatment with sodium hydride/methyl iodide.On reaction with trimethyloxonium tetrafluoroborate, 3 was O-alkylated to yield the title thiazepine 5, the thermal stability of which is compared with that of the isomeric 4-methoxy-1,5-benzothiazepine C.Compound 5 could be oxidized to give the sulfone 6; thermolysis of 5 leads to sulfur and 1-methoxyisoquinoline (8).Alkylation of 5 with methyl iodide/silver tetrafluoroborate yields the sulfonium salt 7 which rearranges to 1-methoxy-4-(methylthio)isoquinoline (9) on heating in acetonitrile.
- Hofmann, Hans,Fischer, Herbert
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p. 2147 - 2150
(2007/10/02)
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- Photochemistry of Methoxy-substituted Quinoline and Isoquinoline N-Oxides
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The photochemistry of quinoline 1-oxides and isoquinoline 2-oxides bearing a methoxy-group in the pyridine ring was investigated in protic and aprotic media.The formation of various photoisomers, viz. 3,1-benzoxazepines, 2(1H)-quinolones, N-(2-isocyanobenzyl)formamides, 4(1H)-quinolones, and 3-hydroxyquinolines from the different methoxyquinoline 1-oxides, and 1,3-benzoxazepines and 1(2H)-isoquinolones from the different methoxyisoquinoline 2-oxides, was observed along with deoxygenation and formation of products derived from hydration and decomposition of the primary products.The position of the methoxy-group has an important directing effect on the photoreactions.
- Albini, Angelo,Fasani, Elisa,Dacrema, Lucia Maggi
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p. 2738 - 2742
(2007/10/02)
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