Efficient Synthesis of 6-(1H-1,2,4-Triazol-1-yl)-thieno[2,3-d]pyrimidin-4(3H)-ones via an Iminophosphorane |
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| Authors: | Yong Sun Nian-Yu Huang |
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| Institution: | 1. Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, Central China Normal University , Wuhan, China;2. Department of Chemistry , Yunyang Teachers College , Danjiangkou Hubei, China;3. Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, Central China Normal University , Wuhan, China |
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| Abstract: | Ethyl 2-amino-4-methyl-5-(1H-1,2,4-triazol-1-yl)thiophene-3-carboxylate 2, obtained from Gewald reaction of 1-(1H-1,2,4-triazol-1-yl)acetone 1 with ethyl cyanoacetate and sulfur, was transferred into iminophosphorane 3. Further reaction of 3 with aromatic isocyanates gave carbodiimides 4, which were treated subsequently with a secondary amine to give 6-(1H-1,2,4-triazol-1-yl)-thieno2,3-d]pyrimidin-4(3H)-ones 6 in good yields in the presence of a catalytic amount of sodium ethoxide. |
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| Keywords: | Aza-Wittig reaction Gewald reaction iminophosphorane thieno[2 3-d]pyrimidin-4(3H)-one 1 2 4-triazole |
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