- Novel Reaction of Uracil Derivatives Possessing Electron-withdrawing Groups at the 5-Position with Amines: Exchange Reaction between the N1-Portion of Uracils and Amines
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The reaction of 1,3-disubstituted uracils possessing an electron-withdrawing group such as nitro, carbamoyl, and cyano at 5-position with primary amines resulted in the exchange of the N1-portion of the uracil ring with the amine moiety.The exchange reactions were influenced by the nature of substituents at the 5- and N1-position.The reaction sequence is explained in terms of addition, ring-opening, and ring-closure.
- Hirota, Kosaku,Kitade, Yukio,Sajiki, Hironao,Maki, Yoshifumi,Yogo, Motoi
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p. 367 - 373
(2007/10/02)
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- NOVEL REACTION OF 5-NITRO(OR CARBAMOYL)URACIL DERIVATIVES WITH AMINES. THERMAL EXCHANGE REACTION OF N1-PORTION OF THE URACILS FOR AMINES VIA RING-OPENING AND RING-CLOSURE PROCESSES
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The reaction of 1,3-disubstituted uracils possessing an electron withdrawing group at the 5-position with amines induced exchange of N1-portion of the uracil ring for amines.This reaction was accelerated by substitution of phenyl groups at the N1-position.
- Hirota, Kosaku,Kitade, Yukio,Sajiki, Hironao,Maki, Yoshifumi
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p. 3263 - 3266
(2007/10/02)
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- Pyrimidine Derivatives and Related Compounds. Part 48. Uracil Ring Transformation: Conversion of 5-Nitrouracils into 5-Carbamoyluracils
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1,3-Disubstituted 5-nitrouracils (1) react with malonamide in ethanolic sodium ethoxide to afford 1-substituted 5-carbamoyluracils (3) via rearrangement of the N(3)-C(4)-C(5) portion of the uracil.This ring transformation has been applied to the preparation of 2',3',5'-tri-O-acetyl-5-carbamoyluridine (8).
- Hirota, Kosaku,Kitade, Yukio,Senda, Shigeo
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p. 1859 - 1861
(2007/10/02)
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