Abstract
Stirring of N-(2-carboxybenzoyl) anthranilic acid with anilines and amines such as p-toluidine, benzylamine, methyl esters of Leu, Phe, Ile and Val in presence of DCC produces N- 2 substituted 3-phenyliminoisoindolinones in very good yields. Single crystal X-ray diffraction studies and solution phase NMR and CD studies reveal that the 3-phenyliminoisoindolinone moiety is a turn-inducing scaffold which should be useful for reverse-turn mimetics.
Highlights
3-iminoisoindolinone derivatives are pigments with excellent color strength and suitable for pigmenting organic materials of high molecular weight, such as ethyl cellulose, acetyl cellulose, nitrocellulose, polyamide, polyester, natural resins and synthetic resins.[1]
3-iminoisoindolinone and its derivatives are important for diverse kinds of applications, there has been only a limited number of methods available in the literature for their synthesis
We thought that N-(2-carboxybenzoyl)anthranilic acid 1, the alkaline hydrolysis product of 2-phthalimidobenzoic acid,[8] could be a reverse-turn inducing scaffold
Summary
3-iminoisoindolinone derivatives are pigments with excellent color strength and suitable for pigmenting organic materials of high molecular weight, such as ethyl cellulose, acetyl cellulose, nitrocellulose, polyamide, polyester, natural resins and synthetic resins.[1]. We were trying to develop reverse-turn mimetics through DCC mediated coupling of 1 with various anilines, amines and amino acids. The formation 2a and 2b in the above method indicates that the natural L-α-amino acids would be good candidates for reaction with 1 in a similar fashion to provide a useful route to achieve reverse-turn mimetics on the basis of a 3-phenyliminoisoindolinone scaffold.
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