Purine N-Oxides. XLIV. The Cyclization of 6-Amino-5-nitrosouracil with Formaldehyde. Preparation and Properties of 7-Hydroxyxanthine

Gury Zvilichovsky; George Bosworth Brown

doi:10.1021/jo00977a002

Purine N-Oxides. XLIV. The Cyclization of 6-Amino-5-nitrosouracil with Formaldehyde. Preparation and Properties of 7-Hydroxyxanthine

Gury Zvilichovsky
, George Bosworth Brown

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

7-Hydroxyxanthine has been obtained from the reaction of one of the tautomeric forms of 6-amino-5-nitro-souracil and formaldehyde. Its 7-acetoxy derivative reacts rapidly with nucleophiles in neutral aqueous solutions to yield 8-substituted xanthines. Similar facile nucleophilic substitutions at position 8 are observed with 3-acetoxyxanthine, and an analogous mechanism via a commnn intermediate is proposed.

Original language	English
Pages (from-to)	1871-1876
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	37
Issue number	12
DOIs	https://doi.org/10.1021/jo00977a002
State	Published - 1 Jun 1972
Externally published	Yes

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N2 - 7-Hydroxyxanthine has been obtained from the reaction of one of the tautomeric forms of 6-amino-5-nitro-souracil and formaldehyde. Its 7-acetoxy derivative reacts rapidly with nucleophiles in neutral aqueous solutions to yield 8-substituted xanthines. Similar facile nucleophilic substitutions at position 8 are observed with 3-acetoxyxanthine, and an analogous mechanism via a commnn intermediate is proposed.

AB - 7-Hydroxyxanthine has been obtained from the reaction of one of the tautomeric forms of 6-amino-5-nitro-souracil and formaldehyde. Its 7-acetoxy derivative reacts rapidly with nucleophiles in neutral aqueous solutions to yield 8-substituted xanthines. Similar facile nucleophilic substitutions at position 8 are observed with 3-acetoxyxanthine, and an analogous mechanism via a commnn intermediate is proposed.

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Purine N-Oxides. XLIV. The Cyclization of 6-Amino-5-nitrosouracil with Formaldehyde. Preparation and Properties of 7-Hydroxyxanthine

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