16735-29-8Relevant academic research and scientific papers
Generation of 1,3-selenaza-1,3-butadienes by thermal cycloreversion of 2,4,6-trisubstituted 6H-1,3,5-oxaselenazines
Shimada, Kazuaki,Aikawa, Kei,Fujita, Takuji,Aoyagi, Shigenobu,Takikawa, Yuji,Kabuto, Chizuko
, p. 701 - 702 (1997)
1,3-Selenaza-1,3-butadienes were generated by thermal cycloreversion of 6H-1,3,5-oxaselenazines, and were trapped with dienophiles or nucleophiles to give the corresponding [4+2] cycloadducts or 1,4-adducts, respectively.
Base-Induced Transformation of 2-Acyl-3-alkyl-2H-azirines to Oxazoles: Involvement of Deprotonation-Initiated Pathways
Ning, Yingtang,Otani, Yuko,Ohwada, Tomohiko
, p. 6313 - 6326 (2017/06/23)
An experimental study of base-induced transformation reaction of 2-acyl-3-alkyl-2H-azirines to oxazoles indicated that a deprotonation-initiated mechanism is involved, in addition to nucleophilic addition to the imine functionality. Calculations suggested
Transition-metal-free oxidative α-C-H amination of ketones via a radical mechanism: Mild synthesis of α-amino ketones
Jiang, Qing,Xu, Bin,Zhao, An,Jia, Jing,Liu, Tian,Guo, Cancheng
, p. 8750 - 8756 (2015/01/08)
A transition-metal-free direct α-C.H amination of ketones has been developed using commercially available ammonium iodide as the catalyst and sodium percarbonate as the co-oxidant. A wide range of ketone ((hetero)aromatic or nonaromatic ketones) and amine (primary/secondary amines, anilines, or amides) substrates undergo cross-coupling to generate synthetically useful α-amino ketones. The mechanistic studies indicated that a radical pathway might be involved in the reaction process. The utility of the method is highlighted through a concise one-step synthesis of the pharmaceutical agent amfepramone.
Flow-vacuum pyrolysis of 2,5-diphenyl-4-methyloxazole
Banciu, Mircea D.,Istrati, Daniela,Schiketanz, Iosif,Mihǎiescu, Dan,Drǎghici, Constantin,Malacea, Raluca
, p. 493 - 499 (2007/10/03)
The flow-vacuum pyrolysis of 2,5-diphenyl-4-methyloxazole (4) at 1000°C and 0.5 Torr afforded a complex reaction mixture containing: benzonitrile, diphenylmethane, 9,10-dimethylphenantrene, 9,10-dimethylantracene, fluorene, o-benzylbenzonitrile (major product, 20-22%), phenanthrene, anthracene, o,o′-dicyanodiphenyl, 9,10-anthraquinone, 2-methyl-4,5-diphenyloxazole and 1,1,2,2-tetraphenylethane. A radical- and carbene mechanism is suggested in order to rationalize the formation of the reaction products.
Generation of 1,3-chalcogenaza-1,3-butadienes by thermal cycloreversion of 2,4,6-trisubstituted 6H-1,3,5-oxachalcogenazines
Shimada, Kazuaki,Aikawa, Kei,Fujita, Takuji,Sato, Masanobu,Goto, Kurara,Aoyagi, Shigenobu,Takikawa, Yuji,Kabuto, Chizuko
, p. 511 - 525 (2007/10/03)
1,3-Thiaza- and 1,3-selenaza- 1,3-butadienes bearing several substituents at the C-2 and C-4 positions were generated through thermal cycloreversion of 6H-1,3,5-oxathiazines or 6H-1,3,5-oxaselenazines, respectively, and the heterodienes were efficiently trapped by using acetylenic dienophiles. When 6H-1,3,5-oxathiazines or 6H-1,3,5-oxaselenazines were heated in the presence of nucleophiles, such as alcohols or thiols, the corresponding 1,4-adducts of the heterodienes with the nucleophiles were obtained in good yields. On the other hand, heating of 6H-1,3,5-oxathiazines or 6H-1,3,5-oxaselenazines in the absence of trapping agents afforded several products which originated from the in situ generated 1,3-chalcogenaza-1,3-butadienes; also the heterodienes were not isolated or observed directly as the monomeric forms at all.
Aminoketone, oxazole and thiazole synthesis. Part XIII. 1 new 2-aryl-6-phenyloxazoles with 4-methyl or 4-isopropyl groups
Schiketanz, Iosif,Istrati, Daniela,Drǎghici, Constantin,Balaban, Alexandru T.
, p. 137 - 142 (2007/10/03)
Benzoylation of (±)-α-alanine and (±)-valine followed by cyclization afforded the corresponding azlactones, which reacted with benzene, toluene, o- and m-xylene yielding substituted N-benzoyl-phenacylamines. Their cyclization in the presence of phosphorus oxychloride led to the title compounds whose electronic and NMR spectra (1H and 13C) are presented.
Pyrrolomorphinans as δ opioid receptor antagonists. The role of steric hindrance in conferring selectivity
Farouz-Grant,Portoghese
, p. 1977 - 1981 (2007/10/03)
A series of 2',3'-disubstituted pyrrolomorphinans (5a-i) were synthesized to determine the role of steric hindrance at μ and γ receptors in promoting δ opioid receptor antagonist selectivity. In smooth muscle preparations, five members of the series (5a-c,e,f) possessed K(e) values in the range 2-15 nM and were 6 selective. Since the unsubstituted analogue 4 possessed δ antagonist potency of similar magnitude, but was not δ selective, it is suggested that the 2',3'substitution confers δ selectivity by hindering the interaction of the pharmacophore at μ and γ receptors, while not affecting δ receptors.
Ephedrine and pseudoephedrine precursors
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, (2008/06/13)
Preparation of novel prochiral olefinic compounds which can be asymmetrically hydrogenated to enantiomers, which are converted to ephedrine and pseudoephedrine by described procedures.
