87321-69-5Relevant articles and documents
Regioselective hetero-Michael addition of oxygen, sulfur, and nitrogen nucleophiles to maleimides catalyzed by BF3·OEt2
An, Yu-Long,Deng, Yun-Xia,Zhang, Wei,Zhao, Sheng-Yin
, p. 1581 - 1592 (2015/03/18)
Abstract A practical BF3·OEt2-catalyzed regioselective 1,2-addition or 1,4-hetero-Michael addition of oxygen, sulfur, and nitrogen nucleo philes to maleimides has been developed for the synthesis of alkyl fumarate derivatives or 3-su
Synthesis of 2,3,4,5-tetra-substituted pyrroles via a base-promoted double Michael reaction of oxime-enoates with nitroolefins
Kuroda, Yusuke,Imaizumi, Kazuto,Yamada, Ken-Ichi,Yamaoka, Yosuke,Takasu, Kiyosei
supporting information, p. 4073 - 4075 (2013/07/26)
A new method of synthesizing 2,3,4,5-tetra-substituted pyrroles from oxime-enoates with nitroolefins is described. This reaction involves a base-promoted double Michael reaction, followed by dehydrative aromatization.
Derivatives of aryl amines containing the cytotoxic 1,4-dioxo-2-butenyl pharmacophore
Jha, Amitabh,Mukherjee, Chandrani,Prasad, Ashok K.,Parmar, Virinder S.,Vadaparti, Manjula,Das, Umashankar,De Clercq, Erik,Balzarini, Jan,Stables, James P.,Shrivastav, Anuraag,Sharma, Rajendra K.,Dimmock, Jonathan R.
supporting information; experimental part, p. 1510 - 1515 (2010/06/16)
Several series of compounds containing the 1,4-dioxo-2-butenyl moiety have been prepared as candidate cytotoxins, including the methyl N-arylmaleamates, methyl N-arylfumaramates, and N-arylmaleimides. In addition, the N-arylisomaleimides were synthesized which are the structural isomers of N-arylmaleimides. These compounds were evaluated against human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 cells. Methyl N-arylfumaramates showed the highest cytotoxic potencies and, in particular, methyl N-(3,4-dichlorophenyl)fumaramate is six times more potent than melphalan towards L1210 cells and is equipotent with this drug in the Molt 4/C8 assay. Electrophilicity of compounds under investigation was demonstrated by carrying out thiolation using model benzyl mercaptan on representative compounds. Methyl N-(3,4-dichlorophenyl)fumaramate and methyl N-(4-chlorophenyl)maleamate inhibited human N-myristoyltransferase, a possible molecular target, in high micromolar range. QSAR and molecular modeling revealed some correlations between different structural features of a number of the molecules and cytotoxic potencies. Methyl N-arylfumaramates were well tolerated in mice in comparison to the analogs in other series of compounds tested. The data obtained in this investigation affords guidelines for preparing new series of molecules with greater potencies.
Synthesis and antifungal activity of N-(alkyl/aryl)-2-(3-oxo-1,4- benzothiazin-2-yl)acetamide
Gupta,Wagh
, p. 697 - 702 (2007/10/03)
A series of N-(alkyl/aryl)-2-(3-oxo-1,4-benzothiazin-2-yl)acetamide have been synthesized by condensation of substituted amines with maleic anhydride (MA) followed by cyclization with o-aminothiophenol (o-ATP). All the compounds have been screened for their antifungal activity against Tricophyton rubrum, Epidermophyton floccosum and Malassazia furfur. In the primary screening, some of the compounds exhibited appreciable activity. The structures of the synthesized compounds 7a-z have been established on the basis of elemental analysis and spectral data.
N-bromosuccinimide-dibenzoyl peroxide/azabisisobutyronitrile: A reagent for Z- to E-alkene isomerization
Baag, Md. Merajuddin,Kar, Anirban,Argade, Narshinha P.
, p. 6489 - 6492 (2007/10/03)
N-Bromosuccinimide-dibenzoyl peroxide/azobisisobutyronitrile is used to carry out several types of Z- to E-alkene isomerizations. The NBS-bromination conditions are sufficient for both allylic bromination and alkene isomerization. When the allylic hydrogens are not available in substrates, only the isomerization of the alkene takes place. The present conditions for isomerization of carbon-carbon double bonds are mild and efficient.
Nickel(0) induzierte und katalysierte CC-Verknuepfungen von Phenylisocyanat mit funktionalisierten Alkenen
Hoberg, Heinz,Guhl, Dieter
, p. 245 - 258 (2007/10/02)
Monosubstituted alkenes RCH=CH2 (R=OEt (Ia), SPh (Ib), CO2Me (Ic)) react with phenyl isocyanate on (Lig)Ni0 systems to form tricyclohexylphosphane-5-azanickelacyclopentan-4-one-derivatives (V).It is shown that the complexes V are intermediates in the catalytic CC coupling reaction.Further reactions by the system is dependent upon the nature of R.Thus when R=OEt (Ia) a β-elimination is induced, which ultimately leads to 3-ethoxyacrylic acid anilide (XIa), the unsaturated product of a 1/1 CC coupling.On the other hand, when R=CO2Me (Ic) further insertion of isocyanate occurs, to give 1,5-diphenyl-2,6-dioxo-hexahydropyrimidine-4-acidmethylester (XII).Characteristic features are descriebed, and the reaction mechanisms are discussed.
