Purines. LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines

The Dimroth rearrangement of 7-alkyl-1-methyladenines (8) to produce 7-alkyl-N6-methyladenines (9) (63-72% yield) has been found to be accompanied with unusual hydrolytic deaminations to give 7-alkyl-1-methylhypoxanthines (10) (1-3.5%) and/or 7-alkylhypoxanthines (11) (12-22%), when effected in boil...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1994/02/15, Vol.42(2), pp.382-384
Hauptverfasser:	FUJII, Tozo, SAITO, Tohru, II, Ryoko, SUZUKI, Tomoko
Format:	Artikel
Sprache:	eng
Schlagworte:	adenine 1, 7-disubstituted Chemistry deamination hydrolytic Dimroth rearrangement Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings hypoxanthine 1, 7-disubstituted hypoxanthine 7-substituted Organic chemistry Preparations and properties
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Beschreibung
Zusammenfassung:	The Dimroth rearrangement of 7-alkyl-1-methyladenines (8) to produce 7-alkyl-N6-methyladenines (9) (63-72% yield) has been found to be accompanied with unusual hydrolytic deaminations to give 7-alkyl-1-methylhypoxanthines (10) (1-3.5%) and/or 7-alkylhypoxanthines (11) (12-22%), when effected in boiling H2O for 4-70 h. Probable pathways leading to these by-products are proposed.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.42.382