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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
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
0040-4020
6909-6917
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.
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), 6909-6917. (doi:10.1016/j.tet.2006.04.093).

Record type: Article

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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More information

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: https://eprints.soton.ac.uk/id/eprint/44361
ISSN: 0040-4020
PURE UUID: 8dc000d1-3987-4ac5-8ba1-0f925f7564a0
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 28 Feb 2007
Last modified: 14 Mar 2019 01:48

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