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Synthesis 2006(23): 3967-3972  
DOI: 10.1055/s-2006-950316
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Purinyl and Pyrimidinyl 1′(N)-Homocarbanucleosides Based on a 1-Methylcyclopenta[c]pyrazole Scaffold; Part 2

Marcos D. García, Olga Caamaño*, Franco Fernández, Xerardo García-Mera, Isabel Pérez-Castro
Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Fax: +34(981)594912; e-Mail: qoolga@usc.es;
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Publication History

Received 10 July 2006
Publication Date:
12 October 2006 (online)

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Abstract

Two new 6-aryl-substituted 1′(N)-homocarbanucleosides were prepared by Suzuki-Miyaura reactions of the protected 6-halopurine derivatives with phenylboronic acids. Additionally, 1′(N)-homocarbanucleosides of 6-chloropurine, 2-amino-6-chloropurine and 3-benzoyluracil were prepared by Mitsunobu reaction with a protected diol. From the uracil derivative, the corresponding 5-bromo- and 5-iodouracil compounds were also obtained.

Key words

synthesis - 1′(N)-homocarbanucleosides - methylcyclopenta[c]pyrazole - Mitsunobu reaction - Suzuki-Miyaura cross-coupling reaction