24042-89-5Relevant academic research and scientific papers
Synthesis of pyrimidine and 1,3-bishydroxylamine derivatives from enone Mannich base methiodides
Khlestkin, Vadim K.,Tikhonov, Alexsei Ya.
, p. 249 - 254 (2002)
Reaction of the bis(aminomethylated) alkylaromatic ketones with methyl iodide gave the enone Mannich base methiodides. Subsequent reaction with two equivalents of methoxyamine or sodium anti-benzaldoximate resulted in 1,3-bismethoxyamine or dinitrone correspondingly. Partial hydroxylaminolyses of dinitrones led to 5-aroyl-1,3-dihydroxy-2-phenylperhydropyrimidines. Reaction of the enone Mannich base methiodides with cyclic paramagnetic amidine gave nitroxides of imidazopyrimidine series.
MANNICH REACTION UNDER HIGH PRESSURE. DIMETHYLAMINOMETHYLATION OF KETONES WITH BIS(DIMETHYLAMINO)METHANE UNDER MILD CONDITIONS
Matsumoto, Kiyoshi,Hashimoto, Shiro,Otani, Shinichi,Amita, Fujitsugu,Osugi, Jiro
, p. 585 - 590 (2007/10/02)
Dimethylaminomethylation of ketones with bis(dimethylamino)methane takes place cleanly in methanol at room temperature in the kiro bar region.
Evaluation of some Mannich bases derived from substituted acetophenones against P-388 lymphocytic leukemia and on respiration in isolated rat liver mitochondria
Dimmock,Shyam,Hamon,Logan,Raghavan,Harwood,Smith
, p. 887 - 894 (2007/10/02)
Series of 3-dimethylamino-1-aryl-1-propanone hydrobromides (IV) and 3-dimethylamino-2-dimethylaminomethyl-1-aryl-1-propanone dihydrobromides (V) were synthesized. Evaluation of these derivatives against P-388 lymphocytic leukemia growth revealed that two compounds show promise as antineoplastic agents. Compounds of the V series were unstable in phosphate buffer (in contrast to series IV), and when the same nuclear substituent was present in both series of compounds, V was ~ 100 times more active than IV in both the stimulation and inhibition of respiration of mitochondria isolated from rat liver cells. Representatives from both series showed that respiration in mitochondria was affected by changing the pH of the aqueous buffer from 7.4 to 6.9 or 6.4 and by reducing the temperature from 37° to 20°. The compounds showed reactivity toward a biomimetic thiol.
Carbon-Carbon Bond Formation by the Use of Chloroiodomethane as a C1 Unit. III. A Convenient Synthesis of the Mannich Base from Enol Silyl Ether by a Combination of Chloroiodomethane and N,N,N',N'-Tetramethylmethanediamine
Miyano, Sotaro,Hokari, Hiroshi,Hashimoto, Harukichi
, p. 534 - 539 (2007/10/02)
The Mannich dimethylaminomethylation of carbonyl compounds is conveniently carried out via enol trimethylsilyl ethers by a combination of chloroiodomethane (CH2ClI) and N,N,N',N'-tetramethylmethanediamine (TMMD) in DMSO as the solvent at ambient temperatute.The mechanism of the transformation is discussed on the basis of product analysis and 1H NMR spectral studies.The reagent system CH2ClI/TMMD also provides a convenient route to the Eschenmoser's salt ().
THE MANNICH REACTION OF CARBONYL COMPOUNDS VIA SILYL ENOL ETHERS BY A COMBINATION OF CHLOROIODOMETHANE AND N,N,N',N'-TETRAMETHYLDIAMINOMETHANE
Miyano, Sotaro,Hokari, Hiroshi,Mori, Akira,Hashimoto, Harukichi
, p. 1213 - 1214 (2007/10/02)
The Mannich dimethylaminomethylation of carbonyl compounds is conveniently carried out via trimethylsilyl enol ethers by a combination of chloroiodomethane and N,N,N',N'-tetramethyldiaminomethane in DMSO or DMF as the solvent at ambient temperature.
