Synthesis of certain Substituted Condensed Pyrimidines

In the present work, the ring systems pyrrolo (1, 2-c) pyramiding and pyrimido (5, 4-e) pyrrolo (1, 2-c) pyridine was prepared. Some of the newly synthesized compounds have shown certain pharmacological activities including analgesic, anti-inflammatory and anticonvulsant effects.2-Dicyanomethylidino -5-methylpyrrolidine (II) was first prepared by reacting the lactim ether intermediate I with malononitrile. The bicyclic system pyrrolo (1,2-c) pyridine III was then obtained from the addition reaction of the dinitrile derivative II to isocyanates or isothiocyanates.Alkylation’s of the amino group in compounds III was achieved using diethyl sulfate to give the 3-alkylimonium alkyl sulfates IV. These compounds yielded the 3-alkylimino derivatives V when treated with an aqueous solution of sodium hydroxide.The 3-amino derivatives VI were obtained from the reduction of their corresponding minorities III with sodium borohydride at room temperature.Hydrolysis of the cyclic amino and aminonitriles III and VI with 18% hydrochloric acid was found to give the 3-oxo analogues VII and VIII without affecting the 4-cyano group. On the other hand, hydration of the 4-cyano group in III and VI to the 4-carboxamide derivatives IX and X respectively, was achieved using 90% sulfuric acid. Further hydrolysis of the amide IX by the Bouveault’s method ended to the formation of the carboxylic acid derivative XII. A series of ester compounds XIII were then prepared from different alcohols, using sulfuric acid as catalyst.