- Re-examination of microwave-induced synthesis of phthalimides
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Solvent-free microwave reactions between phthalic anhydride and amino compounds need at least one liquid phase. The reaction occurs after melting of anhydride and subsequent solubilisation in amines. So, reactions between two solids may not take place and need the use of a high boiling point solvent. In all cases, excellent yields are obtained within short reaction times with products of high purity. (C) 2000 Elsevier Science Ltd.
- Vidal, Thierry,Petit, Alain,Loupy, André,Gedye, Richard N.
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Read Online
- Microwave-Assisted Method for the Synthesis of Perylene Ester Imides as a Gateway Toward Unsymmetrical Perylene Bisimides
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A high yielding microwave-assisted synthetic method to obtain unsymmetrical perylene diester monoimide (PEI) by treating the perylene tetrester (PTE) with a requisite amine is reported. Perylene-based molecules are widely used in the construction of self-assembled supramolecular structures because of their propensity to aggregate under various conditions. In comparison to perylene bisimides (PBIs), PEIs are less studied in organic electronics/self-assembly due to the synthetic difficulty and low yields in their preparation. PEIs are less electron deficient and have an unsymmetric structure in comparison to PBIs. Further, the PEIs have a higher solubility than PBIs. The present method is applicable with a wide range of substrates like aliphatic, aromatic, benzyl amines, PTEs, and bay-annulated PTEs. This method provides a tuning handle for the optical/electronic properties of perylene derivatives and also provides an easy access to unsymmetrical PBIs from the PEIs.
- Gupta, Ravindra Kumar,Achalkumar, Ammathnadu S.
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supporting information
p. 6290 - 6300
(2018/05/29)
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- Continuous Method For Producing Amides Of Aromatic Carboxylic Acids
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The invention relates to a continuous method for producing amides of aromatic carboxylic acids by reacting at least one carbonic acid ester of formula (I) R3—OOOR4, wherein R3 represents an optionally substituted aromatic hydrocarbon group with 5 to 100 carbon atoms and R4 represents a hydrocarbon group with 1 to 30 carbon atoms, with at least one amine of formula (II) HNR1R2, wherein R1 and R2 independently represent hydrogen or a hydrocarbon group with 1 to 100 C atoms, in a reaction tube the longitudinal axis of which extends in the direction of propagation of the microwaves of a monomode microwave applicator, under microwave irradiation to form carboxamide.
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Page/Page column 9; 10
(2012/04/23)
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- 1,2-di-substituted benzene-carboxamide derivative, hair growth promoter and external composition for skin using the same
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A 1,2-di-substituted benzene-carboxamide derivative or a salt thereof expressed by the following Formula (I); wherein each of A and B is R1 or -(CH2)n-NR2R3, wherein when A is R1, B is -(CH2)n-NR2R3 and when A is -(CH2)n-NR2R3, B is R1; Z is -O-, -OCO-, -OCONR6- or -NR6-; R1 is a hydrocarbon group of C10-30; R2 and R3 individually represent a hydrogen atom, a lower alkyl group, a phenyl group or a benzyl group, or together represent a heterocyclic ring having 3-7 members; when A is -(CH2)n-NR2R3, R2 may be a hydrogen atom, a lower alkyl group, a phenyl group or a benzyl group, and R3 and R5 together may represent a heterocyclic ring of 6 or 7 members including two nitrogen atoms; when -Z-B is -OCONR6-(CH2)n-NR2R3 or -NR6-(CH2)n-NR2R3, R2 may be a hydrogen atom, a lower alkyl group, a phenyl group or a benzyl group, and R3 and R6 together may represent a heterocyclic ring of 6 or 7 members including two nitrogen atoms; R4 is selected from the group consisting of a halogen atom, a lower alkyl group, a lower acyl group, a nitro group, a cyano group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a lower alkylamino group, a lower acylamino group, a lower alkoxy group and a lower acyloxy group; R5 is a hydrogen atom, a lower alkyl group, a lower acyl group or a lower alkylcarbamoyl group, or when A is -(CH2)n-NR2R3, R5 and R3 together may represent a heterocyclic ring of 6 or 7 members including two nitrogen atoms; R6 is a hydrogen atom, a lower alkyl group, a lower acyl group or a lower alkylcarbamoyl group, or when -Z-B is -OCONR6-(CH2)n-NR2R3 or -NR6-(CH2)n-NR2R3, R6 and R3 together may represent a heterocyclic ring of 6 or 7 members including two nitrogen atoms; l is an integer of 0-2; and n is an integer of 0-5. The 1,2-di-substituted benzene-carboxamide derivative or the salt thereof has excellent hair growth and regrowth promoting effects, which are useful for care, improvement or prevention of hair loss in mammals and, in particular, in humans.
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- Hypolipidemic activity of phthalimide derivatives. IV: Further chemical modification and investigation of the hypolipidemic activity of N-substituted imides
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A further investigation of N-substituted derivatives of phthalimide for hypolipidemic activity has revealed that the chain length, as well as the type of substitution on the N-alkyl chain of phthalimide is critical for biological activity. In these studies the hypolipidemic activity was not improved by extending the chain length beyond five carbon atoms in the alkyl and alkanoic acid series. Imido nitrogen substitutents, other than alkanoic acids, methyl ketones, and alkyl groups, caused a reduction in hypolipidemic activity, e.g., hydroxy, amino, hydroxymethyl, or carbethoxy. Reduction of the keto group in the side chain to an alcohol, as well as forming derivatives of the keto group, did not improve the hypolipidemic activity with the exception of 1-N-phthalimidobutan-3-one semicarbazone. This compound demonstrated improved hypocholesterolemic activity over phthalimide and 1-N-phthalimidobutan-3-one. Substitution of the 3-position of the aromatic moiety of phthalimide with an amino or nitro group, as well as substituting a pyridine or cyclohexyl ring for the phenyl ring, led to the loss of hypolipidemic activity.
- Chapman Jr.,Cocolas,Hall
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p. 1344 - 1347
(2007/10/02)
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- Process for the production of cyclic carboxylic acid imides
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In a process for reacting an aromatic or hydroaromatic alicyclic or heterocyclic dicarboxylic acid or its anhydride with an aliphatic or aromatic alicyclic or heterocyclic mono- or di-amine to produce an N-substituted dicarboxylic acid imide with a splitting off of water, the improvement of carrying out the reaction in a liquid solvent mixture consisting essentially of a non-polar organic solvent and a strongly polar organic solvent which together form a ternary azeotrope with water at reaction temperatures between about 40°C. and 160°C. The imide products are generally known for use as intermediates and final products in a number of industries.
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