N-substituted Phthalimides Research Articles

ChemInform Abstract: SYNTHESIS OF MEROCYANINE DYES

AbstractAus den Komponenten (I) und (IIIa) bzw. (IV) + (IIIa), (IIIb) bzw. (IV) + (VI) werden die neuen Titelverbindungen (II), (V) und (VII) synthetisiert (IR‐, UV‐Daten).

Synthesis of Merocyanine Dyes

Abstract New 1-ethyl-2-[(2-substituted 3-oxoisoindolin-1-ylidene)methyl]-pyridinium or quinolinium iodide merocyanine dyes were obtained by the reaction of 2-methyl quaternary salts with N-substituted phthalimide in the presence of piperidine. 1-Ethyl-2-[(1-substituted 5-oxo-3-pyrrolin-2-ylidene)methyl] quinolinium iodide merocyanines were also prepared. Structural configuration of the synthesised compounds was confirmed by IR and UV spectral determination. 1-Ethyl-2-[[3-oxo-2-(4-phenylthiazol-2-yl)isoindolin-1-ylidene]methyl]quinolinium iodide has high bactericidal activity againsist E.Coli, Staphylococcus Aureus, and Staphylococcus Albas.

ChemInform Abstract: ALKALINE HYDROLYSIS PRODUCTS OF N‐SUBSTITUTED PHTHALIMIDES

Chemischer InformationsdienstVolume 6, Issue 49 Preparative Organic Chemistry ChemInform Abstract: ALKALINE HYDROLYSIS PRODUCTS OF N-SUBSTITUTED PHTHALIMIDES S. KHAQAN HASAN, S. KHAQAN HASANSearch for more papers by this authorS. AHMAD ABBAS, S. AHMAD ABBASSearch for more papers by this author S. KHAQAN HASAN, S. KHAQAN HASANSearch for more papers by this authorS. AHMAD ABBAS, S. AHMAD ABBASSearch for more papers by this author First published: December 9, 1975 https://doi.org/10.1002/chin.197549175AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume6, Issue49December 9, 1975 RelatedInformation

Alkaline Hydrolysis Products of N-Substituted Phthalimides

Products of alkaline hydrolysis of N-substituted phthalimides are described. Five isomeric compounds, 1,6-diketo-3,4,5,6-tetrahydro-1 H-2,5-benzoxazocine (1), 2-(o-carboxyphenyl)-Δ2 -oxazoline (7), 2-phthalimidoethanol (3), N-vinylphthalamic acid (8), and N-(o-carboxybenzoyl)-aziridine (9), are possible from the alkaline hydrolysis of 2-bromoethylphthalimide (2). Gabriel claimed in 1905 that 1 was formed on alkaline hydrolysis of 2 but later structure 7 was suggested for the product. The interest in the synthesis of 1 has led to a reinvestigation of this hydrolysis and structure 7 is confirmed for the initial product of the hydrolysis but it converts on warming during recrystallization into 1 which affords 3 on heating above melting point.Hydrolysis of 2-chloroethylphthalimide (4) and 2-phthalimidoethyl-p-toluenesulfonate (5) also afforded 7. Attempted preparation of 1 from intramolecular cyclization of 2-hydroxyethylphthalamic acid (11) was not successful and only 3 was obtained.Reaction of phthalic anhydride with 2-aminoethylsulfuric acid (14) at 150 ° afforded diphthalimidoethyl phthalate (13) instead of 2-phthalimidoethylsulfuric acid (6). Isolation of 13 indicates formation of 3 as an intermediate product in this reaction.

The Reaction of N-(Phenylsulfonyl)phthaiimide and N-Mesylphthalimide with Various Amines

The formation of N-substituted phthalimides by the reaction of N-(phenylsulfonyl)phthalimide (PSPI) and N-mesylphtalimide (MSPI) with various amines was investigated. The reaction of PSPI with aniline at room temperature in THF gave the ring-opening adduct, N-phenyl-N (phenylsulfonyl)-phthalamide (1a), whereas that in THF with basic catalysts or in basic solvents afforded N-phenylphthalimide (2). Similarly, N-mesyl-N -phenylphthalamide (1b)and (2) were synthesized from MSPI with aniline. The adducts (1a)and (1b) were converted by heating at 160 C into (2) by the elimination of sulfonamides. PSPI also reacted with various amines in ethanol at 80 C to form N-substituted phthalimides in good yields.

Synthesis of N-Substituted Phthalimides from Phthalic Thioanhydride and Amines

Phthalic thioanhydride reacted with ise-butylamine, benzylamine, cyclohexylamine, b-aminobenzoic acid, P-aminobenzenesulfoAamide, o-aminobenzamide, and o-phenylenediamine in ethanol at 80C, with the evolution of hydrogen suifide, to afford N-substituted phthalimides in good yields.Phthaloylation of glycine, B-alanine, and o-aminobenzoiacid was also achieved under basic reactions conditions. A probable reaction route is disussed.

Five-membered rings. II. Inter and intramolecular reactions of simple amines with N-substituted phthalimides. Methylamine as a reagent for removal of a phthaloyl group from nitrogen

A reexamination of the literature on inter and intramolecular reactions of amines with N-substituted phthalimides has led to the demonstration that methylamine is a convenient reagent for removal of a phthaloyl protecting group from nitrogen at room temperature. Application of this procedure (first described in 1896) to the Gabriel synthesis of primary amines and to peptide synthesis is recommended. The simplicity of the reaction is a consequence of the consecutive occurrence of two unexpectedly rapid processes: (1) methylaminolysis of one of the imide bonds; (2) intramolecular catalysis, by an N-methylamido group, of the hydrolysis or aminolysis of an adjacent phthalamido linkage.Some unsuccessful attempts to prepare 2-aminoethylphthalimide are also described.

Synthesis of seven new polyphenyl ethers

Reaction of Potassium Phthalimide with Sulfonyl Chlorides. All of the compounds listed in Table I were prepared in the same manner. A stirred mixture of 0.0050 mole of potassium phthalimide and 0.0050 mole of the appropriate sulfonyl chloride in 20 ml. of acetonitrile was heated under reflux for 1 hour. After cooling to ambient temperature, the mixture was poured into 100 ml. of cold water. The white solid, which separated immediately, was removed by filtration, washed with water, and dried. The crude products were purified by one or two recrystallizations from the solvents indicated in Table I. Each N-substituted phthalimide was found to be identical with an authentic sample, which was prepared by the reaction of the appropriate sulfonamide with phthaloyl chloride according to the method of Evans and Dehn ( I ) , by mixture melting point determination and infrared spectra comparison. In experiments that involved methaneand butane-lsulfonyl chlorides, small amounts of a solid-32 and 20 mg., respectively-precipitated from the aqueous filtrates on standing overnight. This solid was identified by mixture melting point determination and infrared spectra comparison as phthalimide.

Thalidomide as a Possible Biological Acylating Agent

THE teratogenic activity of thalidomide is now well known, but the mechanism by which the drug produces foetal abnormalities is obscure. Recent investigations in this laboratory1 on the relationship between embryotoxic activity and chemical structure in a series of compounds related to thalidomide (α-phthalimidoglutarimide) suggested that the phthalimide portion of the molecule is important in determining teratogenic activity. Replacement of the phthalimide ring of thalidomide by other ring systems such as those of succinimide and hexahydrophthalimide was found to lead to the loss of embryotoxic activity in tho rabbit. However, replacement of the glutarimide ring of thalidomide by other groups did not in every case lead to complete loss of embryopathic activity, for 4-phthalimidobutyramide, phthalimidobenzene and 2-phthalimidoglutaric acid anhydride were still embryotoxic in rabbits but much less so than thalidomide. These observations suggested that an N-substituted phthalimide structure was essential for embryotoxic activity. However, the exact structural requirements in the N-substituent for embryotoxicity are not yet clear, but, so far as is known at present, optimum embryotoxic activity is found when the N-substituent is α-glutarimide as in thalidomide itself.

Notes- The Sodium Borohydride Reduction of N-Substituted Phthalimides

Notes- The Sodium Borohydride Reduction of N-Substituted Phthalimides

The Bromination of Some N-Substituted Phthalimides with N-Bromosuccinimide

The Bromination of Some N-Substituted Phthalimides with N-Bromosuccinimide

244. Contributions to the chemistry of synthetic antimalarials. Part IV. Hydrazine hydrolysis and radical exchange reactions of N-substituted phthalimides in relation to the constitution of the antimalarial R.63

244. Contributions to the chemistry of synthetic antimalarials. Part IV. Hydrazine hydrolysis and radical exchange reactions of N-substituted phthalimides in relation to the constitution of the antimalarial R.63

The Reaction Between N-Substituted Phthalimides and Primary Amines

WE have shown that treatment of phthalimide with a primary aliphatic amine such as methylamine gives NN-dimethylphthalamide in high yield1. The controlling step in the reaction sequence was found to be the remarkable ease of conversion of N-methylphthal-amide into N-methylphthalimide, which occurs rapidly and quantitatively on shaking with water at room temperature. In view of the recent communication of H. J. Barber and W. R. Wragg2, we now record some observations made in a continuation of our previous work.

Composition of the Antimalarial Drug R.63 and the Ing and Manske Hydrazine Hydrolysis of N-Substituted Phthalimides

DURING 1944, we investigated, as part of our antimalarial research programme, the structure of the potent antimalarial drug R.631. The recent publication by Mosher2 of a further contribution to this subject makes it desirable to report briefly our own results. Some of this work forms the subject-matter of a British Patent Application (17071/44, of September 6, 1944) which was placed on the secret list, thus delaying publication. It is clear that Mosher has independently reached the same conclusion as our own, namely, that R.63 contains a substantial proportion of R.36 (8-β-aminopropylamino-6-methoxyquinoline dihydrochloride).

Toxicity of Some N-Substituted Phthalimides to Codling Moth Larvae

Toxicity of Some N-Substituted Phthalimides to Codling Moth Larvae