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Schiff bases from TRIS and formylpyridines: structure and mechanistic rationale aided by DFT calculations

Schiff bases from TRIS and formylpyridines: structure and mechanistic rationale aided by DFT calculations
Schiff bases from TRIS and formylpyridines: structure and mechanistic rationale aided by DFT calculations
This paper describes the synthesis and structural elucidation of 1,3-oxazolidines derived from tris(hydroxymethyl)aminomethane (TRIS) and pyridine-based aldehydes. Divergent results were obtained with other formylpyridines, such aspyridoxal, in which intramolecular hydrogen-bonding largely stabilizes the iminic structure. The oxazolidines may undergo ring-opening under acetylating conditions to afford imines through different mechanistic pathways, which have also been evaluated by DFT calculations
1434-193X
6224-6232
Martínez, R. Fernando
25456861-d6d7-4964-ac9c-54f5a1e5c2ba
Ávalos, Martín
2d0b39c7-15a3-4f90-bdfb-8e4b6e69c64a
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Pérez, Esther M. S.
1ebe5954-6236-4586-80a2-2bde38783c70
Martínez, R. Fernando
25456861-d6d7-4964-ac9c-54f5a1e5c2ba
Ávalos, Martín
2d0b39c7-15a3-4f90-bdfb-8e4b6e69c64a
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Pérez, Esther M. S.
1ebe5954-6236-4586-80a2-2bde38783c70

Martínez, R. Fernando, Ávalos, Martín, Babiano, Reyes, Cintas, Pedro, Jiménez, José L., Light, Mark E., Palacios, Juan C. and Pérez, Esther M. S. (2010) Schiff bases from TRIS and formylpyridines: structure and mechanistic rationale aided by DFT calculations. European Journal of Organic Chemistry, 2010 (32), 6224-6232. (doi:10.1002/ejoc.201000922).

Record type: Article

Abstract

This paper describes the synthesis and structural elucidation of 1,3-oxazolidines derived from tris(hydroxymethyl)aminomethane (TRIS) and pyridine-based aldehydes. Divergent results were obtained with other formylpyridines, such aspyridoxal, in which intramolecular hydrogen-bonding largely stabilizes the iminic structure. The oxazolidines may undergo ring-opening under acetylating conditions to afford imines through different mechanistic pathways, which have also been evaluated by DFT calculations

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Published date: November 2010

Identifiers

Local EPrints ID: 179427
URI: http://eprints.soton.ac.uk/id/eprint/179427
ISSN: 1434-193X
PURE UUID: 94e62409-82f3-41ab-b39b-b3f24a4208b3
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 01 Apr 2011 10:22
Last modified: 07 Oct 2020 07:23

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Contributors

Author: R. Fernando Martínez
Author: Martín Ávalos
Author: Reyes Babiano
Author: Pedro Cintas
Author: José L. Jiménez
Author: Mark E. Light ORCID iD
Author: Juan C. Palacios
Author: Esther M. S. Pérez

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