caa a22 4500 445876972 CHVBK 20180317145530.0 cr unu---uuuuu 170323e20110801xx s 000 0 eng 10.1007/s10593-011-0804-2 doi (NATIONALLICENCE)springer-10.1007/s10593-011-0804-2 Microwave-assisted N-allylation of uracil and thymine pyrimidine bases [Elektronische Daten] [L. Sacarescu, I. Atudosie, M. Simionescu, G. Sacarescu, V. Harabagiu] This work presents a new synthetic approach to N(1)-allylation of pyrimidine nucleobases with allyl bromide. The increased efficiency of the proposed method is based on two specific elements: (a) the nucleoside N-deprotonation is carried out in a homogeneous system by using sodium methylsulfinyl- methylide in DMSO; (b) the allylation reaction is microwave-assisted. This method ensures high yields (87-88%) of the monoallylated products and short reaction time (1.5h as compared to tens of hours for classical methods), and provides protection against side reactions. NMR analysis of the crude reaction mixture indicated a ratio of 6-8 : 1 between N(1)-allyl derivatives and N(1),N(3)-diallyl derivatives. Springer Science+Business Media, Inc., 2011 nucleobase nationallicence thymine nationallicence uracil nationallicence allylation nationallicence microwave nationallicence Sacarescu L. ˈˈPetru Poniˈˈ Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania aut Atudosie I. ˈˈPetru Poniˈˈ Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania aut Simionescu M. ˈˈPetru Poniˈˈ Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania aut Sacarescu G. ˈˈPetru Poniˈˈ Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania aut Harabagiu V. ˈˈPetru Poniˈˈ Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania aut Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/5(2011-08-01), 602-606 0009-3122 47:5<602 2011 47 10593 https://doi.org/10.1007/s10593-011-0804-2 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10593-011-0804-2 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Sacarescu L. ˈˈPetru Poniˈˈ Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania aut NATIONALLICENCE 700 1- Atudosie I. ˈˈPetru Poniˈˈ Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania aut NATIONALLICENCE 700 1- Simionescu M. ˈˈPetru Poniˈˈ Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania aut NATIONALLICENCE 700 1- Sacarescu G. ˈˈPetru Poniˈˈ Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania aut NATIONALLICENCE 700 1- Harabagiu V. ˈˈPetru Poniˈˈ Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania aut NATIONALLICENCE 773 0- Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/5(2011-08-01), 602-606 0009-3122 47:5<602 2011 47 10593 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer