Abstract
The preparation of a variety of N-substituted 3-azaisatoic anhydrides 3 and 8 is described. These anhydrides reacted with thiopseudoureas to give interesting bicyclic, tricyclic, and tetracyclic heterocycles many of which are new ring systems. One such heterocycle, the imidazo[1,2-a]pyrido[2,3-d]pyrimidine ring system, was studied further with respect to alkylation and reduction reactions. Alkylation of 12h occurred on the nitrogen in the central B ring, whereas, in the reduced species 33, alkylation took place in the C ring. The reaction of 3-azaisatoic anhydrides with carbanions was also investigated. Reactions occur with anions generated from nitromethane, diethylmalonate, ethyl nitroacetate, ethyl isocyanate, and ethyl o-fluorobenz-oylacetate.
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