Synthesis of substituted 3‐(5‐amino‐[1,3,4]thiadiazol‐2‐yl)‐2H‐pyrano[2,3‐c]pyridin‐2‐ones |
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Authors: | Irina O Zhuravel' Sergiy M Kovalenko Alexandre V Ivachtchenko Valentin P Chernykh Pavlo E Shinkarenko |
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Abstract: | An efficient two‐step synthesis of novel 3‐(5‐amino‐1,3,4]thiadiazol‐2‐yl)‐2H‐pyrano2,3‐c]pyridine‐2‐ones was developed. In the first step, a new 2H‐pyrano2,3‐c]pyridine‐3‐carboxamide 5 was prepared by Knoevenagel condensation of pyridoxal hydrochloride with cyanoacetamide. In the second step, the reaction of carboxamide 5 with a series of N4‐substituted thiosemicarbazides yielded a library of 35 dis crete compounds 8 {1–35} in high yields. The intermolecular recyclization mechanism leading to these products is discussed. |
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