Construction of C-nucleosides diversified by [3+2] cycloaddition from a sugar-based mesoionic ring
Construction of C-nucleosides diversified by [3+2] cycloaddition from a sugar-based mesoionic ring
A mesoionic acyclic C-nucleoside (4), serves as the starting chiron to construct highly functionalized 2-aza-7-thiabicyclo[2.2.1]heptanes and heptenes by means of a [3+2] cycloaddition with acetylenic and olefinic dipolarophiles. Further elimination of either sulfur or hydrogen sulfide leads to acyclic C-nucleosides bearing a heterocyclic moiety of 2-pyridone.
1, 3-dipolar cycloaddition, mesoionic heterocycle, c-nucleoside, pyridone, thioisomunchnone anhydro-4-hydroxythiazolium hydroxide system, click chemistry, efficient, dipolarophiles, acid
6909-6917
Arévalo, Maria J.
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Ávalos, Martin
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Babiano, Reyes
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Cintas, Pedro
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Jimenez, José L.
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Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
2006
Arévalo, Maria J.
7f940557-6cf5-4e72-9478-2bc5154fb06b
Ávalos, Martin
63d81458-5377-48ba-9558-b512a8550866
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Jimenez, José L.
c9e89576-0cb3-4e84-a213-fe7617f55521
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Arévalo, Maria J., Ávalos, Martin, Babiano, Reyes, Cintas, Pedro, Jimenez, José L., Light, Mark E. and Palacios, Juan C.
(2006)
Construction of C-nucleosides diversified by [3+2] cycloaddition from a sugar-based mesoionic ring.
Tetrahedron, 62 (29), .
(doi:10.1016/j.tet.2006.04.093).
Abstract
A mesoionic acyclic C-nucleoside (4), serves as the starting chiron to construct highly functionalized 2-aza-7-thiabicyclo[2.2.1]heptanes and heptenes by means of a [3+2] cycloaddition with acetylenic and olefinic dipolarophiles. Further elimination of either sulfur or hydrogen sulfide leads to acyclic C-nucleosides bearing a heterocyclic moiety of 2-pyridone.
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Published date: 2006
Keywords:
1, 3-dipolar cycloaddition, mesoionic heterocycle, c-nucleoside, pyridone, thioisomunchnone anhydro-4-hydroxythiazolium hydroxide system, click chemistry, efficient, dipolarophiles, acid
Identifiers
Local EPrints ID: 44361
URI: http://eprints.soton.ac.uk/id/eprint/44361
ISSN: 0040-4020
PURE UUID: 8dc000d1-3987-4ac5-8ba1-0f925f7564a0
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Date deposited: 28 Feb 2007
Last modified: 16 Mar 2024 03:04
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Contributors
Author:
Maria J. Arévalo
Author:
Martin Ávalos
Author:
Reyes Babiano
Author:
Pedro Cintas
Author:
José L. Jimenez
Author:
Juan C. Palacios
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