Purines. XLVII. Dimroth Rearrangement versus Hydrolytic Deamination of 1-Ethyladenine

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概要

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• The Dimroth rearrangement of 1-ethyladenine (6) to give N^6-ethyladenine (11)(91% yield) was accompanied with unusual hydrolytic deaminations to produce hypoxanthine (8)(2%) and 1-ethylhypoxanthine (14)(2%), when carried out in 0.2N aqueous NaOH at 100℃ for 7h. Probable pathways leading to these by-products are discussed on the basis of the results of alkaline hydrolysis of 5-amino-N'-ethylimidazole-4-carboxamidine dihydrochloride (5), which yielded both 5-aminoimidazoli-4-carboxamide (9) and 5-amino-N-ethylimidazole-4-carboxamide (12). For structural identification, 14 was alternatively synthesized from inosine (17) through 1-ethylinosine (16), and 12 was synthesized from 16 through 5-amino-N-ethyl-1-β-D-ribofuranosylimidazole-4-carboxamide (15). Comparison of the reaction rates in the Dimroth rearrangements of 6・HClO_4 and 1-ethyl-9-methyladenine perchlorate [1・HClO_4 (R^1=Et; R^2=Me)] in H_2O at pH 6.92 and 8.70 (ionic strength 1.0) at 70℃ has revealed that nonsubstitution at the 9-position decreases the rearrangement rate by a factor of 4-30 under these conditions.

• 公益社団法人日本薬学会の論文
• 1990-12-25

著者

• 斎藤 徹

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 澄三

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 久田 裕美

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 久田 裕美

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 新保 孝治

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 藤井 澄三

  Shinshu Univ. Nagano Jpn

• 新保 孝治

  Faculty Of Pharmaceutical Sciences Kanazawa University

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