A novel synthesis of aryl tethered imidazo[4,5-b]pyrazin-2-ones through in situ ring construction and contraction |
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Authors: | Ramendra Pratap Raja Roy |
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Institution: | a Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow 226 001, India b Division of SAIF, Central Drug Research Institute, Lucknow 226 001, India |
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Abstract: | An innovative synthesis of aryl tethered 1,3-dimethylimidazo4,5-b]pyrazin-2-ones 4 and 6 has been delineated through base catalyzed ring transformation of 6-aryl-4-(piperidin-1-yl)-2H-pyran-2-one-3-carbonitriles 1 and methyl 6-aryl-4-methylsulfanyl-2H-pyran-2-one-3-carboxylates 5 with 7-acetyl-1,3-dimethyllumazine 2 with subsequent ring contraction of the fused pyrimidine to an imidazole ring. An additional product, methyl 6-(1,3-dimethyl-2-oxo-2,3-dihydro-1H-imidazo4,5-b]pyrazin-5-yl)-4-thiophen-2-ylpyran-2-ylidene]acetate 8b, was also isolated from the reaction of 5 and 2, as a minor constituent. |
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Keywords: | Imidazo[4 5-b]pyrazine 2H-Pyran-2-ones Ring transformation |
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