Purines. XXXVIII. A General Synthesis of 7, 9-Dialkyladeninium Salts from 9-Alkyladenines by Regioselective Alkylation : Utilization of an N6-Alkoxy Group as a Control Synthon

Tozo FUJII; Tohru SAITO; Teruyo SAKUMA; Masako MINAMI; Isao INOUE

doi:10.1248/cpb.38.652

Purines. XXXVIII. A General Synthesis of 7, 9-Dialkyladeninium Salts from 9-Alkyladenines by Regioselective Alkylation : Utilization of an N⁶-Alkoxy Group as a Control Synthon

藤井澄三, 斎藤徹, 佐久間照世, 南政子, 井上勲

著者情報

キーワード: 7, 9-dialkyladenine synthesis, N⁶-alkoxy-9-alkyladenine, regioselective alkylation, catalytic hydrogenolysis, dealkoxylation, Dimroth rearrangement, amino-imino tautomerism, HPLC analysis, UV, ^1H-NMR

ジャーナルフリー

1990 年 38 巻 3 号 p. 652-660

DOI https://doi.org/10.1248/cpb.38.652

詳細

抄録

A detailed account is given of the general synthetic route to 7, 9-dialkyladeninium salts (16-18) from N⁶-alkoxy-9-alkyladenines (type 5 or 11-13), readily obtainable from 9-alkyladenines in three steps involving N(1)-oxidation, O-alkylation, and Dimroth rearrangement. Alkylations of N⁶-methoxy-9-methyladenine (5) and 9-alkyl-N⁶-benzyloxy-adenines (11-13) with MeI, EtI, and PhCH₂Br in AcNMe₂ produced the corresponding 7-alkylated derivatives (15 and 19-21), together with small amounts of the N⁶-alkylated isomers (6, 8, and 9). Catalytic hydrogenolysis of the former compounds with hydrogen and Raney Ni yielded 7, 9-dialkyladeninium salts (16-18).

責任著者(Corresponding author)

J-STAGEへの登録はこちら（無料）