Dehydration of N-arylmaleamic acids with acetic anhydride

Sauers, Carol K.

doi:10.1021/jo01260a008

Cited by 59 publications

(20 citation statements)

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“…In addition, under our experimental conditions we do not observe the two signals from the isoimide olefinic protons (7.50 and 6.80 ppm with J ¼ 5.5 Hz), highlighted in particular by Sauers on aromatic amines. [22] A characteristic inversion of the methyl peaks was also observed around 1 ppm; indeed, the a protons (at the ends of the chain) are located at 1.4 ppm (0.8 ppm for corresponding diamines), those of the a chain remain at 1.2 ppm. Finally, the signal of the methylene protons on a of the imide group shifted at 4.3 ppm as was expected.…”

Section: Synthesis and Characterization Of Bismaleimidesmentioning

confidence: 89%

Photopolymerization without Photoinitiator of Bismaleimide‐Containing Oligo(oxypropylene)s: Effect of Oligoethers Chain Length

Vázquez¹,

Joly‐Duhamel²,

Boutevin³

2009

Macro Chemistry & Physics

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This article describes the synthesis and characterization of a series of poly(propylene glycol bismaleimide) (PPGM) with molecular weights ($\overline M _{{\rm ws}}$) in the range of 390–2 600 g · mol−1. Their photopolymerization rates without photoiniator were similar to that of an acrylate resin in the presence of a photoinitiator. The reactivities and degrees of conversion of these PPGM oligomers, thermal and mechanical properties of the resulting materials were studied as a function of $\overline M _{\rm w}$. Rigid materials were obtained except for that containing the longest PPGM, which exhibited mechanical properties of a rubber. The glass transition temperature values and the thermal stability were found to decrease when $\overline M _{\rm w}$ of used oligomers was increased. Crosslinking density was the parameter that controlled both mechanical and thermal properties.

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Section: Synthesis and Characterization Of Bismaleimidesmentioning

confidence: 89%

Photopolymerization without Photoinitiator of Bismaleimide‐Containing Oligo(oxypropylene)s: Effect of Oligoethers Chain Length

Vázquez¹,

Joly‐Duhamel²,

Boutevin³

2009

Macro Chemistry & Physics

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“…Approximately 10% sample solutions in DMSO-d 6 were prepared in 5 mm tubes with samples referred to tetramethylsilane. Chemical shifts (ppm) and coupling constants (Hz) were obtained by …”

Section: H Andmentioning

confidence: 99%

“…5,6 Reaction of maleic or succinic anhydride with the appropriate arylamine in the presence of anhydrous tetrahydrofuran at room temperature generated the corresponding N-substituted arylsuccinamic (1a-j) or arylmaleamic (2a-p) acids in nearly quantitative yields (94-98%). The starting materials were subsequently transformed to the corresponding N-arylimides (3a-g and 4a-i) by heating them in acetic anhydride with an equimolecular amount of sodium acetate.…”

Section: General Procedures For the Synthesis Of N-substituted Arylmalmentioning

confidence: 99%

¹ H and ¹³ C NMR spectra for a series of arylmaleamic acids, arylmaleimides, arylsuccinamic acids and arylsuccinimides

et al. 1999

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“…The dehydration of 1a – h led to 5a – h under thermodynamically controlled conditions and 6a – h when the reaction was controlled kinetically. 13,14 Reaction of various aryl amines with fumaryl chloride led to the isolation of the corresponding N -arylfumaramic acids 3a – i which were esterified with methanol leading to 4a – i . Condensation of aniline with succinic anhydride produced the corresponding acid 7 from which the ester 8 and dehydrated product 9 were obtained.…”

mentioning

confidence: 99%

Derivatives of aryl amines containing the cytotoxic 1,4-dioxo-2-butenyl pharmacophore

Jha

Mukherjee

Prasad

et al. 2010

Bioorganic & Medicinal Chemistry Letters

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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.

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Dehydration of N-arylmaleamic acids with acetic anhydride

Cited by 59 publications

References 1 publication

Photopolymerization without Photoinitiator of Bismaleimide‐Containing Oligo(oxypropylene)s: Effect of Oligoethers Chain Length

Photopolymerization without Photoinitiator of Bismaleimide‐Containing Oligo(oxypropylene)s: Effect of Oligoethers Chain Length

¹ H and ¹³ C NMR spectra for a series of arylmaleamic acids, arylmaleimides, arylsuccinamic acids and arylsuccinimides

Derivatives of aryl amines containing the cytotoxic 1,4-dioxo-2-butenyl pharmacophore

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Dehydration of N-arylmaleamic acids with acetic anhydride

Cited by 59 publications

References 1 publication

Photopolymerization without Photoinitiator of Bismaleimide‐Containing Oligo(oxypropylene)s: Effect of Oligoethers Chain Length

Photopolymerization without Photoinitiator of Bismaleimide‐Containing Oligo(oxypropylene)s: Effect of Oligoethers Chain Length

1 H and 13 C NMR spectra for a series of arylmaleamic acids, arylmaleimides, arylsuccinamic acids and arylsuccinimides

Derivatives of aryl amines containing the cytotoxic 1,4-dioxo-2-butenyl pharmacophore

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¹ H and ¹³ C NMR spectra for a series of arylmaleamic acids, arylmaleimides, arylsuccinamic acids and arylsuccinimides