Regioselective Condensation of Alkylidenephosphoranes to N-Methoxy- and N-Anilino-1H isoindole-1,3-(2H)-diones |
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Authors: | Wafaa M Abdou Rizk E Khidre Reham F Barghash |
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Institution: | 1. Chemical Industries Division, National Research Centre , Giza , Egypt wabdou@link.net;3. Chemical Industries Division, National Research Centre , Giza , Egypt |
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Abstract: | Treatment of 2-methoxyisoindoline-1,3-dione with resonance-stabilized alkylidenephosphoranes afforded the corresponding monoalkenes as the sole reaction product, in ~58–63% yields, whereas more than 80% yields of the same monoolefin products were obtained when the reactions were carried out under microwave conditions. Similarly, 2-(phenylamino)isoindoline-1,3-dione reacted under either thermal or microwave conditions to give only the corresponding monoalkene derivatives. The alkene products from both substrates were further reduced to the corresponding isoindoles using Zn-dust in EtOH. Prediction of the designed compounds and the in vivo anti-inflammation activity of the products in the rat adjuvant model were also studied. The work is the first demonstration of the anti-inflammatory activity of phthalimide derivatives. |
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Keywords: | Alkylidenephosphoranes inflammatory inhibition N-substituted phthalimides olefination |
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