Functionalized monomers based on N-(4-hydroxy phenyl)maleimide

N-(4-Hydroxy phenyl)maleimide (HPMI) is functionalized with acryloyl, methacryloyl, allyl, propargyl and cyanate groups and the structures of the materials are characterized by FTIR, ¹H NMR and ¹³C NMR. Thermal curing behaviours of the monomers and thermal stabilities of the polymers are studied using thermal analysis. Introduction of polymerizable groups shifts the curing exotherm to low temperatures, and the curing behaviour is dictated by the polymerizable substituent present in the aromatic ring. Polymer from acryloyl-functionalized monomer shows the highest thermal stability (402 °C), whereas the highest char value (49 % at 700 °C) is noted for the polymer obtained from propargyl-functionalized monomer. Polymers derived from functionalization of HPMI with acryloyl and methacryloyl showed better thermal stabilities. Thermosets formed by the thermal polymerization of HPMI functionalized with propargyl and cyanate groups showed higher char values at 700 °C in nitrogen atmosphere.     

Synthesis and Polymerization of N-(L-Menthylcarboxylatomethyl)maleimide

A new type of optically active N-(L-menthylcarboxylatomethyl)maleimide (MGMI) was synthesized from maleic anhydride, glycine, and L-menthol. Radical homopolymerization of MGMI was performed at 50°C for 24 h to give optically active polymer having [α]_D = -57°. Radical copolymerizations of MGMI (M ₁) were performed with styrene (ST, M ₂), methyl methacrylate (MMA, M ₂) in benzene at 50°C. From the results, the monomer reactivity ratios (r ₁, r ₂) and the Alfrey-Price Q, e values were determined as follows: r ₁ = 0.16, r ₂ = 0.006 for the MGMI-ST system; r ₁ = 0.15, r ₂ = 1.65 for the MGMI-MMA system, and Q ₁ = 0.72, e ₁ = 1.59 calculated from the MGMI-MMA system. Anionic homopolymerizations of MGMI were also carried out. Chiroptical properties of the polymers were investigated.     

N-(11-羧基十一烷基)马来酰亚胺及其三聚体的合成

以顺丁烯二酸酐和12-氨基十二酸为原料,硫酸、三乙胺为脱水催化剂,经两步反应合成了N-(11-羧基十一烷基)马来酰亚胺.再在三苯基膦和苯酚作用下,N-(11-羧基十一烷基)马来酰亚胺进一步发生三聚反应合成了相应的马来酰亚胺三聚体.采用红外光谱和核磁共振谱对三聚体的结构进行了表征.     

Photometric determination of N-(p-nitrophenyl)maleimide

A procedure has been developed for the photometric determination of N-(p-nitrophenyl)maleimide based on the formation of a salt of the acinitro form of N-(p-nitrophenyl)maleic acid monoamide, which is formed on the hydrolysis of maleimide in concentrated acetic acid. Maleimide is dissolved in concentrated acetic acid, and the obtained solution is neutralized with an alkali. A bright yellow color of the reaction product appears.     

Synthesis of new heterocyclic compounds based on n-benzyl(heptyl)-3-benzyl(heiityl)amino-4hydroxybutanamide

New derivatives of 1, 3-oxazolidine, 1,3-oxazolidin-2-one, 1,2,3-oxathiazolidin-2-one, and morpholine-2,3-dione respectively, containing the CH₂CONHR group, have been prepared by Me reactions of N-benzyl(heptyl)-3benzyl(hepiyl amino-4-hydroxybutanamide with 5-iodofurfural, ethyl trichloroacetate, thionyl chloride, and diethyl oxalate. The biological activity of the new compounds has been studied.Kuban State Technical University, Krasnodar 350072. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 711–716, May, 1996. Original article submitted January 29, 1996.     

N－（4－烯丙氧基苯基）马来酰亚胺的合成

Ｎ－取代马来酰亚胺与双马来酰亚胺的混合物可制备耐热性高、工艺性好的热固性高分子材料。本文通过对氨基酚与乙酸肝的反应，再通过酚羟基的醚化反应和乙酰氨基的水解反应，并与顺丁烯二酸酐进行酰亚胺化成环反应，合成并鉴定了标题化合物。     

Liquid crystal alignment and pretilt angle generation on a photopolymer layer based on N-(phenyl)maleimide

A photopolymer based on N-(phenyl)maleimide was synthesized and the liquid crystal (LC) alignment effects of the photopolymer layer on homeotropic alignment were studied. Good LC alignment with UV exposure of PMI5CA (N-(phenyl)maleimide with a 5-carbon chain cinnamoyl group) was obtained. However, defective LC alignment was observed for PMI3CA (N-(phenyl)maleimide with a 3-carbon chain cinnamoyl group) and PMIF (N-(phenyl)maleimide including a fluoro-cinnamoyl group). Good LC alignment with UV exposure on the PMI5CA surface was observed with annealing temperature up to 150°C. It seems that the LC aligning ability of the photopolymer layers based on N-(phenyl)maleimide depends on the side chain length of the photopolymer.     

Liquid crystal alignment and pretilt angle generation on a photopolymer layer based on N-(phenyl)maleimide

A photopolymer based on N-(phenyl)maleimide was synthesized and the liquid crystal (LC) alignment effects of the photopolymer layer on homeotropic alignment were studied. Good LC alignment with UV exposure of PMI5CA (N-(phenyl)maleimide with a 5-carbon chain cinnamoyl group) was obtained. However, defective LC alignment was observed for PMI3CA (N-(phenyl)maleimide with a 3-carbon chain cinnamoyl group) and PMIF (N-(phenyl)maleimide including a fluoro-cinnamoyl group). Good LC alignment with UV exposure on the PMI5CA surface was observed with annealing temperature up to 150°C. It seems that the LC aligning ability of the photopolymer layers based on N-(phenyl)maleimide depends on the side chain length of the photopolymer.     

Synthesis and polymerization of N-[4-N′- (α-methylbenzyl)aminocarbonylphenyl]maleimide

A novel type of optically active N-[4-N′-(α-methylbenzyl)aminocarbonylphenyl]maleimide [(R)-MBCP] was synthesized from maleic anhydride, p-aminobenzoic acid, and (R)-methylbenzylamine. Radical homopolymerization of (R)-MBCP was performed in tetrahydrofuran (THF) at 50 and 70°C for 24 h to give optically active polymers having [α]²⁵_D = -141° and -129°, respectively. Anionic polymerization of (R)-MBCP with n-butyllithium in THF and N,N-dimethylformamide gave an optically active polymer having ?78 to ?81° of [α]²⁵_D. Radical copolymerizations of (R)-MBCP (M₁) were performed with styrene (ST, M₂) and methyl methacrylate (MMA, M₂) in THF at 50°C. The monomer reactivity ratios (r₁, r₂) and the Alfrey-Price Q-e values were determined as follows: r₁ = 0.009, r₂ = 0.091, Q₁ = 1.30, e₁ = 1.87 in the (R)-MBCP-ST; r₁ = 0.27, r₂ = 1.21, Q₁ = 0.93, e₁ = 1.46 in the (R)-MBCP-MMA system. Chiroptical properties of the polymers were also investigated. © 1992 John Wiley & Sons, Inc.     

Synthesis,characterization and antibacterial studies of some new tellurated azo compounds

A series of tellurated azo compounds [i.e. (4-HOC₆H₄N=N-Ar)TeBr₃ and (4-HOC₆H₄N=N-Ar)₂TeBr₂, where Ar=5-BrC₆H₃, 5-CH₃C₆H₃ and 5-NO₂C₆H₃] were prepared by the reaction of the corresponding 2-(4-hydroxyphenylazo)aryl mercury chloride with tellurium tetrabromide in 1:1 and 2:1?mole ratio, respectively in dry dioxane as a solvent. The reduction of (4-HOC₆H₄N=N-Ar)TeBr₃ by hydrazine hydrate gave the corresponding ditelluride (i.e., (4-HOC₆H₄N=N-Ar)₂Te₂). Treatment of (4-HOC₆H₄N=N-Ar)₂TeBr₂ with hydrazine hydrate afforded the corresponding tellurides, (4-HOC₆H₄N=N-Ar)₂Te), in good yields. The structures of all newly synthesized compounds were assigned on the basis of their elemental and spectroscopic data. The antibacterial activity of tellurated azo compounds along with mercurated azo compounds was tested with agar diffusion method against the bacteria strains Staphylococcus aureus and Escherichia coli. The antibacterial activities of tellurated azo compounds were in some cases equal or better than those of the reference drug. The mercurated azo compounds were found to be the more antibacterial activity of than those of tellurated azo compounds.     

Synthesis and characterization of new poly(N-1-adamantylmaleimide) and poly(N-1-diamantylmaleimide)

N-l-Diamantylmaleimide was synthesized by reaction of maleic anhydride with 1-aminodiamantane, followed by dehydration with acetic anhydride and sodium acetate. Poly(N-1-adamantylmaleimide) ( IIa ) and poly(N-l-diamantylmaleimide) ( IIb ) were polymerized using 2,2′-azobisisobutyronitrile (AIBN) as an initiator under different experimental conditions such as various initiator concentrations, solvents, polymerization temperatures, and polymerization times. Polymerizations of N-l-adamantylmaleimide in benzene at 60°C or in bulk gave polymers with molecular weights (2000–9500). The experimental results indicated that the propagation may be interrupted by steric hindrance of bulky and rigid substituents such as the adamantyl or diamantyl groups. In addition, the effect of chain transfer to monomer contributes to the relatively low activation energy. The glass transition temperatures of Ia and Ib were 204 and 216°C, respectively. The temperatures at 5% weight loss of the polymers IIa and IIb were above 412°C. © 1996 John Wiley & Sons, Inc.     

Synthesis,biochemical evaluation and computational simulations of new cytochrome bc1 complex inhibitors based on N-(4-aryloxyphenyl) phthalimides

A series of N-(4-aryloxyphenyl)phthalimides were synthesized and identified as new inhibitors of the cytochrome bc1 complex. Furthermore, results obtained from computational simulations indicated that 3e' should bind to the Q_o site of the bc1 complex.     

Synthesis of （p-Formylphenyl）azo Calix[4]arenes

Five novel azo calix[4]arenes were reported. The p-aminobenzaldehyde was diazotized with sodium nitrite in aqueous hydrochloride solution. Mono-, bis-, tris- and tetrakis(p-formylphenyl)azo calix[4]arenes (including proximal and distal isomers) were obtained respectively by diazo-coupling in different molar ratio to calix[4]arene(1) under pH=7.5--8.5 at 0-5℃. All (p-formylphenyl)azo calix[4]arenes were characterized by ^1H NMR, ^13C NMR, IR, MS (ESIMS) spectroscopies and elemental analysis.     

Synthesis of New (Arylsulfanyl)maleimide Derivatives

Russian Journal of Organic Chemistry - Previously unknown 2-(arylsulfanyl)-3-hydroxymaleimide and 2-(arylsulfanyl)-3-chloromaleimide derivatives have been synthesized, and several synthetic...     

Quaternary azo compounds based on adenine derivatives

The structure of quaternary azo compounds containing an azo group and an acrylic acid residue attached to the exocyclic nitrogen atom of adenine is proposed for the products of coupling of N⁶-furfuryladenine with resorcinol, orcinol, and m-cresol after reaction of N⁶-furfuryladenine with nitrous acid on the basis of the UV, PMR, and IR spectral data and the results of electrochemical reduction.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 986–990, July, 1976.The author sincerely thanks his co-workers of the Institute of Organic Synthesis of the Academy of Sciences of the Latvian SSR, V. T. Glezer and Yu. Yu. Popelis for their valuable assistance in this research.     

对二氟甲氧基乙酰苯胺的制备新工艺

对二氟甲氧基乙酰苯胺(1)是一种重要的药物中间体,可用于多种医药、农药等的合成,如用于新型胃药及除虫菊类杀虫剂的合成,尤其进入80年代以来,许多专利报道其用于新药合成[1～6].     

Syntheses and thermostabilities of N-[4-(N′-substituted aminocarbonyl)phenyl]maleimide polymers

Three types of novel N-[4-(N′-substituted aminocarbonyl)phenyl] maleimide (RPhMI: N-substituent (R) = phenyl, cyclohexyl, and cyclododecyl) were synthesized and homopolymerized under several conditions. In the copolymerizations of RPhMI (M₁) with styrene (ST; M₂) or methyl methacrylate (MMA; M₂), monomer reactivity ratios and Alfrey-Price Q, e values were determined. All homopolymers decomposed without softening and melting points. The initial degradation temperatures (T_d) of poly(RPhMI)s were over 320°C. The glass transition temperatures (T_g) of RPhMI copolymers were much higher than those of N-phenylmaleimide (PhMI)–ST, PhMI–MMA, N-cyclohexylmaleimide (CHMI)–ST, and CHMI–MMA copolymers. Thermal stability of the terpolymers of RPhMI with ST and acrylonitrile (AN) was higher than that of ST–AN copolymers, i.e., AS resin. © 1998 John Wiley & Sons, Inc. J. Polym. Sci. A Polym. Chem. 36: 2001–2012, 1998