Pyrimidines. 18. A novel pyrimidine to benzene ring transformation reaction. Conversion of 5-nitro-2 (1H)-pyrimidinone into p-nitrophenol derivatives

…, TL Su, LM Stempel, K Watanabe

文献索引：Fox, Jack J.; Su, Tsann-Long; Stempel, Lloyd M.; Watanabe, Kyoichi A. Journal of Organic Chemistry, 1982 , vol. 47, # 6 p. 1081 - 1084

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被引用次数: 23

摘要

5-Nitro-2 (lH)-pyrimidinone (1) underwent acid-catalyzed condensation with acetone and ethyl acetoacetate to form 4-ketonyl-5-nitropyrimidines 2 and 10 which were readily converted into p-nitrophenol (3) and 5-nitrosalicyclic acid (ll), respectively, by NaOH treatment. Condensation of 1 with butanone gave a pair of diastereomeric adducts 7 and 8. Upon base treatment both 7 and 8 afforded 4-nitrocresol (9). Acid-catalyzed reaction of 1 ...