Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/15301

TitleOne-pot regioselective synthesis of 2,6,9-trisubstituted adenines
Author(s)Dias, Alice
Senhorães, Nádia
Conde, Luís
Proença, M. Fernanda R. P.
Keywordsheterocycles
cyclization
ring closure
ring opening
imidazole
purine
Issue date4-Jan-2011
PublisherThieme Medical Publishers
JournalSynlett
Abstract(s)A series of 2,6,9-substituted adenines were obtained from the easily accessible 5-amino-4-cyanoformimidoyl imidazoles 1, acetic and benzoic anhydrides and primary alkyl amines in a three-steps sequence. Acylation of 1 followed by addition of the amine led to the intermediates 5-amino-4-(N-acyl)formamidino imidazoles 4/5, under mild conditions. Cyclization of 4/5 under reflux in ethanol led to the desired substituted adenine. A preliminary stepwise study led to the development of three general and efficient one-pot methods for the synthesis of adenine derivatives. The one-pot three-step reaction in the presence of DMAP was the most convenient syn-thetic approach.
TypeArticle
URIhttp://hdl.handle.net/1822/15301
DOI10.1055/s-0030-1259289
ISSN0936-5214
Peer-Reviewedyes
AccessRestricted access (UMinho)
Appears in Collections:CDQuim - Artigos (Papers)

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