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

21 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

Access to Document

10.1021/jo00977a002

Cite this

@article{0fb3ac08c65e43f996a1d370f682d6d7,

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

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.",

author = "Gury Zvilichovsky and Brown, {George Bosworth}",

year = "1972",

month = jun,

day = "1",

doi = "10.1021/jo00977a002",

language = "אנגלית",

volume = "37",

pages = "1871--1876",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

T1 - Purine N-Oxides. XLIV. The Cyclization of 6-Amino-5-nitrosouracil with Formaldehyde. Preparation and Properties of 7-Hydroxyxanthine

AU - Zvilichovsky, Gury

AU - Brown, George Bosworth

PY - 1972/6/1

Y1 - 1972/6/1

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.

UR - http://www.scopus.com/inward/record.url?scp=0015512509&partnerID=8YFLogxK

U2 - 10.1021/jo00977a002

DO - 10.1021/jo00977a002

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

C2 - 5037453

AN - SCOPUS:0015512509

SN - 0022-3263

VL - 37

SP - 1871

EP - 1876

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this