SYNTHESIS OF NEW AZOMETHINES BASED ON 3,5-DIALKYL-3,4-DIHYDROTHIENO[2,3-d]PYRIMIDINE-6-CARBOHYDRAZIDE

Abstract

In the present study, a series of new azomethine derivatives based on 3-propyl-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carbohydrazide was synthesized via condensation with various substituted aromatic aldehydes. The reactions were carried out in water at room temperature in the presence of 1–2 drops of concentrated hydrochloric acid as a catalyst. Condensation of carbohydrazide with aromatic aldehydes afforded the corresponding hydrazones containing a C=N linkage. The structures of the synthesized compounds were confirmed by IR and NMR spectroscopic analyses. The IR spectra displayed characteristic bands assigned to the azomethine (C=N) stretching vibrations, whereas the 1H NMR spectra revealed signals corresponding to the azomethine proton (CH=N). The results obtained indicate that 3-propyl-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carbohydrazide is a promising precursor for the directed synthesis of novel functionalized thienopyrimidine derivatives with potential relevance for further biological studies.

References

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2. Eslam M.H. Ali, Mohammed S. Abdel-Maksoud, Chang-Hyun Oh. (2019). Thieno[2,3-d]pyrimidine as a promising scaffold in medicinal chemistry: Recent advances.Bioorganic & Medicinal Chemistry.[Crossref]

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