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Synthesis of certain fused pyrrolothieno[3, 2-e] pyrazine derivatives with possible anxiolytic activity

Mohga M.Badran, Samhia M.A.Roshdy, Mohammed K.Abd El-Hameid

The work comprise the synthesis of some newly 4- substitutedopyrrolothienopyrazines (XIV) with possible anxiolytic effect by either cyclization of urea derivatives (XI) with phosphorus oxychloride or by reaction of 4-chloropyrrolothienopyrazine (XII) with morpholine. Also,4-alkoxy pyrrolothienpyrazines (XIII) was prepared by heating of pyrrolothienopyrazin-4(5H)-one (VIII) with phosphorus oxychloride to afford 4-chloropyrrolothienopyrazine (XII)which upon reactionwith certain alcohols in presence of sodiummetal yielded alkoxy pyrrolothienpyrazines (XIII). Boiling of either compound (IV) or the azide (VII) with odichlorobenzene afforded pyrrolothienopyrazine-4(5H) one (VIII). in different yields Reaction of the acid hydrazide (VI) with sodiumnitrite and concentrated hydrochloric acid afforded the newacyl azide (VII). Refluxing the acid (III) with thionyl chloride produced the intermediate 2-(pyrrol-1- yl)3-thiophene carbonyl chloride (V) which upon heating with hydrazine hydrate gave the desired acid hydrazide (VI). Reaction of 2-(pyrrol-1-yl)-3- thiophene carboxylic acid (III) with ethyl chloroformate, triethylamine and diphenyl phosphoryl azide (DPPA) afforded the unexpected urea derivative (IV). Open field test was done to determine changes of animal behaviors and as screening for antipsychotic activity for some of the prepared compounds, thus it can be concluded that some of the prepared compounds showed central sedative effects and possible anti-anxiety activity.