Purines. XXIX. Syntheses of 9-Alkyl-2-deuterio-N^6-methoxyadenines and 2-Deuterio-N^6,9-dimethyladenine : Tautomerism in 9-Substituted N^6-Alkoxyadenines(Organic,Chemical)

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概要

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• Cyclizations of the alkoxyamidines 7a, i with formic acid gave N^6-methoxy-9-methyladenine (8a) and 9-benzyl-N^6-methoxyadenine (8i). Replacement of formic acid by formic-d acid-din these cyclizations afforded the 2-deuterated species 13a and 13i. A similar cyclization of 22, obtained from 21 by alkaline hydrolysis, with formic-d acid-d yielded 2-deuterio-N^6-methoxy-1,9-dimethyladenine (24). The N^6-methyl isomer 19 was prepared from 13a by treatment with NaH and Mel. Comparison of the proton nuclear magnetic resonance (^1H-NMR) spectrum of 8a in Me_2SO-d_6 with that of 13a revealed that 8a exists as an equilibrated 1:3.5 mixture of the amino (type 14 or 15) and the imino (type 16 or 17) forms. The deuterated species 19 and 24 were utilized for interpretation of the ^1H-NMR spectra of the amino-form model 18 and the imino-form model 23. The existence of amino-imino tautomerism in 8a was also supported by ultraviolet and infrared spectroscopic evidence. Such tautomerism, with a preference for the imino form, in Me_2SO-d_6 was found to be common to 13 other 9-substituted N^6-alkoxyadenines (type 8) including adenosine analogues. On the other hand, comparison of the ^1H-NMR spectra of 11, N^6,9-dimethyladenine (12), and N^6,N^6,9-trimethyladenine (36) indicated that 12 exists solely in the amino form in CDCl_3 or Me_2SO-d_6.

• 公益社団法人日本薬学会の論文
• 1987-11-25

著者

• 板谷 泰助

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 板谷 泰助

  金沢大学薬学部

• 熊澤 幸成

  Faculty of Pharmaceutical Sciences, Kanazawa University

• Saito T

  Research And Development Headquarters Hokurikit Seiyaku Co. Ltd.

• 中嶋 悟視

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 木津 京子

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 木津 京子

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 澄三

  Shinshu Univ. Nagano Jpn

• 中嶋 悟視

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 熊澤 幸成

  Faculty Of Pharmaceutical Sciences Kanazawa University

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