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Features of aminolysis of 2-(3,5-dioxo-4-azathreecyclo[5.2.1.02,6-endo]dec-8-en-4-yl)-butanoic acid anhydride

Yaroslav S. Bondarenko

Abstract


The synthesis of new amide and imide derivatives of 2-(3,5-dioxo-4-azatricyclo[5.2.1.02,6‑endo]-dec-8-en-4-yl)butanedioic acid is described. The title amides were synthesized via corresponding diacid anhydride, which was treated with various amines. It has been shown that aminolysis with p-toluidine selectively delivers a single product, namely 2-(3,5-dioxo-4-azatricyclo[5.2.1.02,6-endo]dec-8-en-4-yl)-4-oxo-4-(p-tolylamino)butanedioic acid. This selectivity can be explained by the charge distribution in the starting anhydride and by larger LUMO coefficient on one of the carbonyl groups. One of the title amido acids could be converted into the corresponding cyclic imide by refluxing in pyridine. This imide is a close structural analog of thalidomide.   

Keywords


aspartic acid; amido acid; regiochemistry; AM1

References


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DOI: http://dx.doi.org/10.15421/081306

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