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■ Synthesis of 3-Amino-4-benzoylsydnones

Wilhelm Fleischhacker* and Ernst Urban

*Institute of Pharmaceutical Chemistry, University of Vienna, Währinger Strasse 10, A-1090 Vienna, Austria

Abstract

In a three step synthesis starting from ethyl hyarazinoacetate HCl (1), 3-benzylidenaminosydnone (4) was available in good yields. Reduction with sodium boranate gave 3-benzylaminosydnone (5a). Lithiation and electrophilic substitution of 5a was studied. Reacting lithiated 5a with N,N-dimethylbenzamide afforded 3-benzylamino-4-benzoylsydnone (5i) which could be deprotected to give 3-amino-4-benzoylsydnone (8b).