23724-93-8Relevant academic research and scientific papers
Organic Superbase t-Bu-P4 Catalyzes Amination of Methoxy(hetero)arenes
Shigeno, Masanori,Hayashi, Kazutoshi,Nozawa-Kumada, Kanako,Kondo, Yoshinori
supporting information, p. 5505 - 5508 (2019/08/01)
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
On the thermally induced rearrangement of 2-alkoxypyridines to N-alkylpyridones
Lister, Troy,Prager, Rolf H.,Tsaconas, Michael,Wilkinson, Kerry L.
, p. 913 - 916 (2007/10/03)
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.
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
Hofmann, Hans,Fischer, Herbert
, p. 2147 - 2150 (2007/10/02)
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.
Photochemistry of Methoxy-substituted Quinoline and Isoquinoline N-Oxides
Albini, Angelo,Fasani, Elisa,Dacrema, Lucia Maggi
, p. 2738 - 2742 (2007/10/02)
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.
