1973
DOI: 10.1021/jo00942a015
|View full text |Cite
|
Sign up to set email alerts
|

Chemistry of some-5-(2-hydroxyalkyl)uracil derivatives and a synthesis of 5-vinyluracil

Abstract: From 5-(2-hydroxyethyl)uracil, its 2-0-methanesulfonate or 2'-0-p-toluenesulfonate, treated with acid or base, a variety of substitution or elimination products can be obtained, depending on the conditions used. Mechanisms for interand intramolecular nucleophilic substitutions, and their competition with elimination of the C-2' groups, are discussed. The decarboxylation of Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1

Citation Types

1
20
0

Year Published

1973
1973
2009
2009

Publication Types

Select...
5
2

Relationship

0
7

Authors

Journals

citations
Cited by 32 publications
(21 citation statements)
references
References 16 publications
(24 reference statements)
1
20
0
Order By: Relevance
“…The base-catalyzed intramolecular cyclization reaction of 3a to 6, as illustrated in Scheme 2, is analogous to the reported conversion of 5-[2-[(methylsufonyl)oxy]ethyl]uracil to 2,3-dihydrofurano[2,3-4-pyrimidin-6(5H)-one using t-BuOK in DMSO (9). The mechanism responsible for the formation of the bicyclic compound 5 proceeds via an elimination reaction involving expulsion of HN3 from 6 as illustrated in Scheme 3 since treatment of 6 with a saturated solution of NH, in MeOH gave the bicylic derivative 10, rather than the azido compound 11 (see Scheme 1).…”
supporting
confidence: 59%
See 3 more Smart Citations
“…The base-catalyzed intramolecular cyclization reaction of 3a to 6, as illustrated in Scheme 2, is analogous to the reported conversion of 5-[2-[(methylsufonyl)oxy]ethyl]uracil to 2,3-dihydrofurano[2,3-4-pyrimidin-6(5H)-one using t-BuOK in DMSO (9). The mechanism responsible for the formation of the bicyclic compound 5 proceeds via an elimination reaction involving expulsion of HN3 from 6 as illustrated in Scheme 3 since treatment of 6 with a saturated solution of NH, in MeOH gave the bicylic derivative 10, rather than the azido compound 11 (see Scheme 1).…”
supporting
confidence: 59%
“…The in vitro antiviral activities of 5-(1-azidoviny1)-(7), 5-[2-(1-azirinyl)]-2'-deoxyuridine (9), and the related bicyclic For personal use only. (10) provided compounds that were inactive in the in vitro assays against HSV-1, HSV-2, VZV, and CMV.…”
Section: Oacmentioning
confidence: 99%
See 2 more Smart Citations
“…[12,15,16] as described in Scheme 1. The sugar moiety of compounds 2b and 3b was protected with toluoyl group after the glycosylation reaction of the hydroxyl-bearing nucleobases 2a and 3a with 1-chloro-3,5-ditoluoyl-2-deoxypentofuranose (chlorosugar).…”
Section: Synthesis Of the Phosphoramiditesmentioning
confidence: 99%