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Stereospecific alkylation of substituted adenines by the mitsunobu coupling reaction under microwave-assisted conditions
dc.contributor.author | García Rubiño, María Eugenia | |
dc.contributor.author | Núñez Carretero, María Del Carmen | |
dc.contributor.author | Choquesillo Lazarte, Duane | |
dc.contributor.author | García Ruiz, Juan Manuel | |
dc.contributor.author | Madrid, Yolanda | |
dc.contributor.author | Campos Rosa, Joaquín María | |
dc.date.accessioned | 2014-05-23T07:11:50Z | |
dc.date.available | 2014-05-23T07:11:50Z | |
dc.date.issued | 2014 | |
dc.identifier.citation | García-Rubiño, M.E.; et al. Stereospecific alkylation of substituted adenines by the mitsunobu coupling reaction under microwave-assisted conditions. RSC Advances, (2014). [http://hdl.handle.net/10481/31881] | es_ES |
dc.identifier.issn | 2046-2069 | |
dc.identifier.uri | http://hdl.handle.net/10481/31881 | |
dc.description.abstract | A novel and efficient synthetic method has been developed for the preparation of alkylated aminopurines (N,N-dimethyl-, 2-chloro-N-methyl-, and N-methyladenines) with achiral and chiral 3,4-dihydro-2H-1,5-benzoxathiepin-3-ol by the Mitsunobu reaction under microwave-assisted conditions. This reaction reveals a complete inversion of the stereogenic centre of the secondary alcohol giving an alkylated purine linked to a homochiral six-membered ring. Fifty novel purine derivatives have been prepared. Alkylation sites have been determined by 2D NMR techniques and for three compounds have been confirmed by X-ray crystallography. The N-9/N-3 regioselectivity can be justified by the electronic effects of the substituents at positions 2 and 6 of the purine. | es_ES |
dc.description.sponsorship | This study was supported by the Instituto de Salud Carlos III (Fondo de Investigación Sanitaria) through the project no. PI10/00592 and by the ERDF (European Regional Development Fund). The M. E. G. R. FPU grant AP2007 02954 from the Ministerio de Ciencia e Innovación of Spain is greatly acknowledged. The project "Factoría de Cristalización" Consolider Ingenio 2010 (CSD2006 00015) provided X ray structural facilities for this work. | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | Royal Society of Chemistry | es_ES |
dc.rights | Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/3.0/ | es_ES |
dc.subject | Alkylated aminopurines | es_ES |
dc.subject | Mitsunobu reaction | es_ES |
dc.subject | X-ray crystallography | es_ES |
dc.title | Stereospecific alkylation of substituted adenines by the mitsunobu coupling reaction under microwave-assisted conditions | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es_ES |
dc.identifier.doi | 10.1039/C4RA01968G |