Purines. VI. Reactions of 2-Chloro- and 2-(Methylsulfonyl)-9-phenyl-9H-purines with Nucleophiles(Organic,Chemical)

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The reactions of 2-chloro-9-phenyl-9H-purine (1) with sodium methoxide, ethoxide, and phenoxide as O-nucleophiles, with butylamine and piperidine as N-nucleophiles, and with sodium methylsulfide as an S-nucleophile, afforded 2-inethoxy (3a), 2-ethoxy (3b), 2-phenoxy (3c), 2butylamino- (4a), 2-piperidino- (4b), and 2-methylthio-9-phenyl-9H-purine (5), respectively. Compound 1 also reacted with ethyl cyanoacetate and phenylacetonitrile as C-nucleophiles in the presence of sodium hydroxide in dimethyl sulfoxide to give ethyl α-cyano-9-phenyl-9H-purine-2-acetate (6a) and α,9-diphenyl-9H-purine-2-acetonitrile (6b). However, 1 did not react with other active methylene compounds, ketones or potassium cyanide. On the other hand, 2-(methylsulfonyl)-9-phenyl-9H-purine (2), prepared easily from 1, smoothly reacted not only with active methylene compounds but also with ketones and potassium cyanide. When active methylene compounds, such as ethyl cyanoacetate and phenylacetonitrile, were used, 2 gave 6a and 6b in good yields. In the cases of ketones and potassium cyanide, the substitution reactions of 2 proceeded to give the corresponding 2-substituted 9H-purines (7 and 8a-d), as expected.

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Details 詳細情報について

  • CRID
    1571698602254946688
  • NII Article ID
    110006281755
  • NII Book ID
    AA00602100
  • ISSN
    00092363
  • Text Lang
    en
  • Data Source
    • CiNii Articles

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