30057-93-3Relevant academic research and scientific papers
Mechanism of nitration of nitrogen-containing heterocyclic N-acetonyl derivatives. General approach to the synthesis of N-dinitromethylazoles
Semenov,Shevelev,Bruskin,Kanishchev,Baryshnikov
, p. 2077 - 2096 (2009)
A general synthetic procedure for the synthesis of N-dinitromethyl derivatives of nitrogen-containing heterocycles has been developed. The procedure includes the destructive nitration of heterocyclic N-acetonyl derivatives of tetrazoles, 1,2,4- and 1,2,3-triazoles, pyrazoles, imidazoles and their bicyclic analogs, as well as imides of carboxylic and sulfonic acids and substituted hydrazines with mixtures of sulfuric and nitric acids. The kinetic study of the reaction mechanism was performed using UV and NMR spectroscopy. It was found that the NO2 groups were sequentially introduced into the methylene fragment by the addition of the nitronium ion to multiple bonds of intermediate enols followed by hydrolysis of the acetyl moiety. The rate and direction of the enolization (due to the CH2 and CH3 groups) of the N-acetonyl compounds in sulfuric acid solutions were determined by the study of the deuterium exchange kinetics. The synthesis of the N-dinitromethyl compounds is complicated by side reactions, such as the decomposition of intermediate α-nitroketone, the nitration of the methyl group in the acetonyl moiety, and the nitration of the dinitromethyl products to trinitromethyl derivatives.
NBu4NI-Catalyzed oxidative imidation of ketones with imides: Synthesis of α-amino ketones
Lv, Yunhe,Li, Yan,Xiong, Tao,Lu, Yu,Liu, Qun,Zhang, Qian
supporting information, p. 2367 - 2369 (2014/03/21)
nBu4NI-Catalyzed oxidative imidation of ketones and imides for the synthesis of α-amino ketones were realized for the first time. The methodology is characterized by its wide substrate scope even for acetone with readily available phthalimide, saccharin and succinimide, which opens a new pathway for direct imidation of ketones. The Royal Society of Chemistry 2014.
Self-assembled bidentate ligands for ru-catalyzed anti-Markovnikov hydration of terminal alkynes
Chevallier, Floris,Breit, Bernhard
, p. 1599 - 1602 (2008/02/02)
(Figure Presented) In pairs: Bidentate ligands are generated by the self-assembly of monodentate ligands through complementary hydrogen bonding. A ruthenium complex bearing such self-assembled heterodimeric ligands is used as the catalyst in the regioselective hydration of terminal alkynes. FG = functional group, Piv = pivaloyl.
Use of Chloroalkenylamines for the Synthesis of 1-Azabicyclooctane and 1-Azabicyclononane Derivatives
Lochead, Alistair W.,Proctor, George R.,Caton, Michael P. L.
, p. 2477 - 2489 (2007/10/02)
Various N-(chloroprop-2-enyl)-, N-(3-chlorobut-2-enyl)-, N-(4-chloropent-3- and -4-enyl)-proline derivatives, -succinimides, and -phthalimides have been synthesised and subjected to Lewis acid treatment.The following gave fruitful results: N-(4-chloropent-3-enyl)-5-hydroxy-2-pyrrolidone (25) gave 1-acetyl-1,2,3,6,7,7a-hexahydropyrrolizin-5-one (28); N-(4-chloropent-3-enyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (30) gave 1-endo-acetyl-1,2,3,9b-tetrahydropyrroloisoindol-5-one (31) which was isomerised to the exo-isomer; N-(4-chloropent-3-enyl)-3-methylene-2,3-dihydro- 1H-isoindol-1-one (34) and N-(4-chloropent-3-enyl)-3-hydroxy-3-methyl-2,3-dihydro-1H-isoindol-1-one (33) gave 1-endo-acetyl-9b-methyl-1,2,3,9b-tetrahydropyrroloisoindol-5-one (35); N-proline (42) gave 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrroloisoquinoline (43), N-(2-chloroprop-2-enyl)-2-(2-hydroxy-2-propyl)pyrrolidine (44) gave 6-chloro-8,8-dimethyl-1,2,3,5,8,8a-hexahydroindolizine (47) and 8,8-dimethyl-1,2,3,7,8,8a-hexahydroindolizin-6(5H)-one (48) which were reduced to the corresponding alcohols; N-(4-chloropent-4-enyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (50) gave 7,8,11,11a-tetrahydro-5H-azepinoisoindole-5,10(9H)-dione (51).
