Purines. LXXIX. Synthesis and Hydrolysis of 3-Methoxyadenine and Its N6-Benzyl Derivative Leading to the Corresponding 2-Hydroxyadenines

Methylation of adenine 3-oxide (8a) with MeI in AcNMe2 afforded 3-emthoxyadenine (9a) in 44% yield. This compound (9a) underwent hydroxide-ion attack at the 2-position to give 2-hydroxyadenine (isoguanine) (10a) in 38% yield. A parallel reaction sequence starting from N6-benzyladenine 3-oxide (8c) a...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1999/04/15, Vol.47(4), pp.554-556
Hauptverfasser:	ITAYA, Taisuke, KANAI, Tae, TAKADA, Yasutaka, KANEKO, Miki, YASUHARA, Kensuke, FUJII, Tozo
Format:	Artikel
Sprache:	eng
Schlagworte:	3-methoxyadenine hydrolysis adenine 3-oxide methylation Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings isoguanine synthesis N6-benzyl-3-methoxyadenine hydrolysis Organic chemistry Preparations and properties
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Zusammenfassung:	Methylation of adenine 3-oxide (8a) with MeI in AcNMe2 afforded 3-emthoxyadenine (9a) in 44% yield. This compound (9a) underwent hydroxide-ion attack at the 2-position to give 2-hydroxyadenine (isoguanine) (10a) in 38% yield. A parallel reaction sequence starting from N6-benzyladenine 3-oxide (8c) and proceeding through N6-benzyl-3-methoxyadenine (9c) provided N6-benzyl-2-hydroxyadenine (10c) in 29% overall yield, together with a small amount of N6-benzyladenine (11c).
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.47.554