Purines. XXVII. : Hydrolytic Deamination versus Dimroth Rearrangement in the 9-Substituted Adenine Ring : Effect of an ω-Hydroxyalkyl Group at the 1-Position
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概要
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In H_2O at near neutrality, the 1-(ω-hydroxyalkyl)adenine derivatives 8a, b・HBr and 8c・HClO_4 underwent hydrolytic deamination to give the 1-(ω-hydroxyalkyl)hypoxanthine derivatives 10a-c, in competition with the usual Dimroth rearrangement to produce the N^6-(ω-hydroxyalkyl)adenine derivatives 9a-c. The rates of these competitive reactions were measured in H_2O at various pH's and ionic strength 1.0 at 40℃, and the relative rate of deamination with respect to Dimroth rearrangement was found to increase as the pH of the reaction medium was decreased. Under similar conditions, the corresponding 1-alkyl analogues 8d-g・HClO_4 and the 1-(modified benzyl) analogues 8h, i・HBr underwent only Dimroth rearrangement to afford the N^6-isomers 9d-i. In the Dimroth rearrangements of all of the substrates 8a, b, d-i・HX (X=Br or ClO_4), attack of hydroxide ion on the protonated species (8a, b, d-i・H^+) at the 2-position was faster than that on the neutral species by a factor of 100-640. In the reaction of the protonated species, the 1-(ω-hydroxyalkyl) analogues 8a, b・HBr rearranged faster than the corresponding 1-alkyl analogues 8e, f・HClO_4 by a factor of 1.6-2.7. It has been concluded that this rate enhancement is attributable solely to the electron-withdrawing effect, and not to intramolecular participation in catalysis, of the hydroxy group in the 1-substituent chain. In the syntheses of 8a, i・HBr from 9-ethyladenine (6) according to a general 1-alkylation procedure, the 7-alkylated products 13 and 16 were also obtained as by-products in 9% and 6% yields, respectively.
- 公益社団法人日本薬学会の論文
- 1986-03-25
著者
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斎藤 徹
Faculty Of Pharmaceutical Sciences Kanazawa University
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藤井 澄三
Faculty Of Pharmaceutical Sciences Kanazawa University
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寺原 典彦
Faculty Of Pharmaceutical Sciences Kanazawa University
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藤井 澄三
Shinshu Univ. Nagano Jpn
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