Easy synthesis of new series of pteridine analogs: di- and tetra-hydropyrimido[4,5-d]pyrimidines via 5-pyrimidinecarbaldehydes

Authors
de la Torre, José M.; Nogueras, Manuel; Borkowski, Eduardo Jorge; Suvire, Fernando D.; Enriz, Ricardo Daniel; Cobo, Justo
Publication Year
2014
Language
English
Format
article
Status
Published version
Description
Pyrimidine-5-carbaldehyde derivatives, of easy access, were selected as precursors for the synthesis of mimic pteridine derivatives 5,6-dihydropyrimido[4,5-d]pyrimidines and 5,6,7,8- tetrahydropyrimido[4,5-d]pyrimidines via 4-amino-(5-aminomethyl)pyrimidine intermediates. Straightforward procedures allow a quick access to these compounds. The dihydro derivatives were prepared means of a final cyclocondensation carried out with orthoesters, catalysed by acid and assisted by microwaves irradiation under solvent free conditions. The final cyclocondensation with carbonyl compounds forming the tetrahydro derivatives was done under mild conditions, in which stereochemical induction was carried out on the building of this skeleton, and stereochemistry assignments corroborated by theoretical calculations.
Fil: de la Torre, José M.. Universidad de Jaén; España
Fil: Nogueras, Manuel. Universidad de Jaén; España
Fil: Borkowski, Eduardo Jorge. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Suvire, Fernando D.. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Enriz, Ricardo Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Cobo, Justo. Universidad de Jaén; España
Subject
4-Amino-5-(aminomethyl)pyrimidines
Microwave irradiation; ; ; cyclocondensation;
Theoretical calculations
Acid catalysis
Cyclocondensation
Stereoselectivity
Química Orgánica
Ciencias Químicas
CIENCIAS NATURALES Y EXACTAS
Access level
Open access
License
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repository
CONICET Digital (CONICET)
Institution
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identifier
oai:ri.conicet.gov.ar:11336/14627