Synthesis of 5-/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular Chemistry
Entity
UAM. Departamento de Química OrgánicaPublisher
Wiley-VCH VerlagDate
2015-11-01Citation
10.1002/ejoc.201501026
European Journal of Organic Chemistry 2015.32 (2015): 7160-7175
ISSN
1434-193X (print); 1099-0690 (online)DOI
10.1002/ejoc.201501026Funded by
Funding from the European Research Council (ERC-StG 279548) and MINECO (CTQ2011-23659) is gratefully acknowledged. V.V.-G. is grateful for a F.P.I. fellowship from MINECO.Project
info:eu-repo/grantAgreement/EC/FP7/ 279548Editor's Version
DOI: http://dx.doi.org/10486/10.1002/ejoc.201501026Subjects
Alkylation; Cross-coupling; Nitrogen heterocycles; Nucleobases; Self-assembly; Supramolecular chemistry; QuímicaNote
This is the peer reviewed version of the following article: European Journal of Organic Chemistry 2015.32 (2015): 7160-7175, which has been published in final form at http://dx.doi.org/10486/10.1002/ejoc.201501026Rights
© 2015 Wiley-VCH Verlag GmbH andCo. KGaA, WeinheimAbstract
A series of lipophilic nucleobases that are substituted at the 5- (pyrimidines) or 8- (purines) position with either a halogen atom or a terminal triple bond have been synthesized. The sequences and reactions studied in this work, which mainly comprise halogenation, alkylation, Sonogashira coupling, and trimethylsilylacetylene deprotection, have been carefully optimized, to reach the final compounds in the most straightforward and convenient way, with the highest possible purity and yield. These compounds include cytosine, isocytosine, and uracil derivatives as pyrimidine heterocycles, and guanine, isoguanine, and 2-aminoadenine derivatives as complementary purine bases. Variability was introduced at the N-1/N-9 positions of these pyrimidine/purine nucleobases, which were functionalized with alkyl or benzyl groups, as well as with protected amine or carboxylic acid substituents. The molecules prepared constitute a useful collection of synthetic intermediates for the field of chemical self-assembly. A series of lipophilic nucleobases substituted at the 5- (pyrimidines) or 8-position (purines) with either a halogen atom or a terminal triple bond have been synthesized. These molecules comprise a useful collection of synthetic intermediates for the field of chemical self-assembly
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Google Scholar:Bilbao, Nerea
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Vázquez-González, Violeta
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Aranda, M. Teresa
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González Rodríguez, David
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