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Synthesis 2004(4): 583-589  
DOI: 10.1055/s-2004-815968
PAPER
© Georg Thieme Verlag Stuttgart · New York

Microwave-Assisted Ring Opening of Epoxides with Pyrimidine Nucleobases: A Rapid Entry into C -Nucleoside Synthesis

A. Khalafi-Nezhad*, M. N. Soltani Rad, A. Khoshnood
Department of Chemistry, College of Science, Shiraz University, Shiraz 71454, Iran
Fax: +98(711)2280926; e-Mail: khalafi@chem.susc.ac.ir;
Further Information

Publication History

Received 11 November 2003
Publication Date:
12 February 2004 (online)

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Abstract

Microwave irradiation strongly accelerates the regio­selective nucleophilic ring opening of epoxides by pyrimidine nucleobases. In the presence of tetrabutylammonium bromide (TBAB), various bases were elaborated to determine the proper base in which it can activate N1 rather than N3 for alkylation. It was shown that MgO not only could serve as an eligible base, but also enhanced the selectivity and tendency of N1 for alkylation as compared with N3. The use of microwave irradiation provided dominant regioselective synthesis of N1-β-hydroxyalkylpyrimidines in moderate to good yields with a reaction time of less than 7 minutes.

Key words

microwave - uracil - epoxides - TBAB - magnesium oxide­

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6

Rodriguez, H.; Perez, R.; Suarez, M.; Lam, A.; Cabrales, N.; Loupy, A. Fifth International Electronic Conference on Synthetic Organic Chemistry (ESCOC-5); http://www.mdpi.net/escoc-5/e0004/e0004.html