Synthesis of Imidazo [4,5-e]-as-triazine (6-Azapurine) Derivatives
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概要
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Synthesis of some derivatives in the novel ring system, imidazo [4,5-e-as]-triazine (6-azapurine) (Va-f), has been described. 2-Benzyl-6-bromo-as-triazine-3,5 (2H, 4H)-dione (1-benzyl-5-bromo-6-azauracil) (I) reacted smoothly with ammonia and benzylamine, to give 6-amino-(IIa) and 6-benzylamino-2-benzyl-as-triazine-3,5 (2H, 4H)-dione (IIb) respectively. Selective thionation of these amino derivatives (IIa, b), by heating with phosphorus pentasulphide in pyridine, to lead to 6-amino-(IIIa) and 6-benzylamino-2-benzyl-as-triazin-3 (2H)-one-5 (4H)-thione (IIIb), effectively proceeded, and subsequent aminodethiolation of the latter (IIIa, b) also readily went on to afford 5,6-diamino-(IVa), 5-amino-6-benzylamino-(IVb), 5-benzylamino-6-amino-(IVc), and 5,6-dibenzylamino-2-benzyl-as-triazin-3 (2H)-one (IVd). An oxidative mode of cyclisation, by heating with ethyl orthoformate or benzaldehyde in nitrobenzene under reflux for a few hours, furnished a successful procedure for the preparation of 2-benzyl-5H-(Va) and 2,5-dibenzyl-imidazo [4,5-e]-as-triazin-3 (2H)-one (Vb), or 2-benzyl-5H-(Vc), 2,5-dibenzyl-(Vd), and 2,7-dibenzyl-6-phenyl-imidazo [4,5-e]-as-triazin-3 (2H)-one (Ve), respectively. An attempted benzylation of Vc yielded a mixture of the products which consisted of Vd, as a minor component, and the alternative isomer assigned tentatively to 2,4-dibenzyl-6-phenyl-imidazo [4,5-e]-as-triazin-3 (2H)-one (Vf), as a major one, however, it was not contaminated with any isolable amount of Ve.
- 公益社団法人日本薬学会の論文
- 1976-09-25
著者
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河瀬 雅美
Department Of Medicinal Chemistry And Pharmaceutical Chemistry School Of Pharmacy The University Of
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鍛冶 健司
Gifu Pharmaceutical University
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河瀬 雅美
Gifu College of Pharmacy
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鍛冶 健司
Gifu College Of Pharmacy
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