Stereospecific alkylation of substituted adenines by the mitsunobu coupling reaction under microwave-assisted conditions
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AutorGarcía Rubiño, M. Eugenia; Núñez Carretero, María del Carmen; Choquesillo-Lazarte, Duane; García Ruiz, Juan Manuel; Madrid, Yolanda; Campos, Joaquín
Royal Society of Chemistry
Alkylated aminopurinesMitsunobu reactionX-ray crystallography
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]
PatrocinadorThis 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.
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.