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Abstract
Phthalimide formation of Phthalic anhydride with various amines using microwave or without a method with the difference of the catalyst used in a prepared Phthalimide, either structure general are C6H4CONRCO and used as starting materials in synthesis several compounds derivative phthalimides are an important compounds because spectrum wide biological activities including Antimicrobial activity, anticonvulsant activity, Anti-inflammatory activity,Analgesic activity, Anti-influenza activity and Thromboxane inhibitory activity.
Keywords: Phthalimide derivatives, biological activity
Introduction
Phthalimides is derivative of phthalic acid(1)and considered of bicyclic nonaromatic nitrogen heterocycles(2), the compounds have pharmacological activities such as analgesic, anti-inflammatory, anti-depressant etc.(3) because structural features for their activity are as: hydrophobic aryl ring, a hydrogen bonding domain,an electron-donor group, another distal hydrophobic site(4), Also enter many application industrial polymer synthesis as anticorrosion(5).
Mechanism of imide formation , through a nucleophilic attack of amino group to anhydride moiety, as in scheme(1) (6):
Synthesis of N- substituted phthalimide method:
1)Traditional procedure
The reaction of Phthalic anhydride and primary amines in acetic acid by using (10 %) sulphamic acidcatalyst at (110 CC) give is N-substituted phthalimides 86-98%(7) .
Synthesis 4-(1,3-dioxoisoindolin-2-yl)benzaldehyde: A solution of 4-aminobenzaldehyde was prepared in dichloromethane and was added dropwise of phthalic anhydride in CH2Cl2 was stirred for 8hr. at (15-20)°C ,After added to mixture sodiumbicarbonat,H2O and removed the solvent under reduced pressure to obtain a residue58%. the mixture poured in crushed ice and filter then crystallized in ether.(8)
Anthranilic acid with phthalic anhydndes and heated in paraffin oil at 130°C-150°C.The resulting filtered and dned it in oven at 60°C then recrystallization was using ethanol with good yield (9).
Phthalic anhydride and fluoren-9(9aH)-ylidene) hydrazine in acetic acid for 4 hour The product was hot filtered and the solvent evaporated and recrystallized from ethanol with obtained result 79%.(5)
2)Using microwave
Reaction phthalic anhydride with amine in microwave with heated at 150-250 °C for 3-10 minutes. The product was recrystallized using Ethanol and yield (89-52%) (10).
Synthesis of compounds2of phthalic anhydride and hydroxylamine hydrochloride in pyridine was MWI for 1min, After cooling solution was poured on to ice/ HCl, filtered off and recrystallized frome thanol,\While compounds 3 Phthalic anhydride and urea was fused under...