Synthesis and Structure of Novel Thieno[2, 3‐d]Pyrimidine Derivatives Containing 1, 3, 4‐Oxadiazole Moiety |
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Authors: | Yuh‐Wen Ho Maw‐Cherng Suen |
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Affiliation: | Department of Materials and Textiles, Nanya Institute of Technology, Jhongli, Taiwan 32091, R.O.C. |
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Abstract: | The reaction of 5‐(1‐pyrrolyl)‐4‐methyl‐2‐phenylthieno[2, 3‐d]pyrimidine carbohydrazide 5 with CS2 in the presence of pyridine afforded the 6‐(2, 3‐dihydro‐2‐mercapto‐1, 3, 4‐oxadiazol‐5‐yl)‐4‐methyl‐5‐(1‐pyrrolyl)‐2‐phenylthieno[2, 3‐d]pyrimidine 6 , which reacted with methyl iodide in the presence of sodium methoxide to yield the 6‐(2‐methylthio‐1, 3, 4‐oxadiazol‐5‐yl)‐4‐methyl‐5‐(1‐pyrrolyl)‐2‐phenyl‐thieno[2, 3‐d]pyrimidine 7. The 6‐(2‐substituted‐1, 3, 4‐oxadiazol‐5‐yl)‐2‐phenylthieno[2, 3‐d]pyrimidine derivatives 9, 11 and 13 were obtained by the condensation of 6‐(2‐methylthio‐1, 3, 4‐oxadiazol‐5‐yl)‐2‐phenylthieno[2, 3‐d]pyrimidine 7 with appropriate secondary amines. The structure of the new compounds was substantiated from their IR, UV‐vis spectroscopy, 1H NMR, mass spectra, elemental analysis and X‐ray crystal analysis. |
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Keywords: | Thioxopyrimidine 1, 3, 4‐Oxadiazole Thieno[2, 3‐d]pyrimidine Spectral characteristics X‐ray crystal structure |
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