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Synthesis 2004(17): 2863-2868  
DOI: 10.1055/s-2004-831252
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Heterocyclic Compounds by Ring Transformations of 2-Formyl Pentose Glycals

Ahmed Baria, Holger Feista, Dirk Michalikb, Manfred Michalik*b, Klaus Peseke*a
a Universität Rostock, Fachbereich Chemie, Albert-Einstein-Str. 3a, 18051 Rostock, Germany
Fax: +49(381)4986412; e-Mail: klaus.peseke@chemie.uni-rostock.de;
b Leibniz-Institut für Organische Katalyse, Buchbinderstr. 5-6, 18055 Rostock, Germany
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Publication History

Received 1 July 2004
Publication Date:
07 October 2004 (online)

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Abstract

2-Formyl-d-xylal 2a and 2-formyl-l-arabinal 2b were reacted with hydrazines to furnish the 4-[1,2-bis(benzyloxy)-3-hydroxypropyl]-1H-pyrazoles 3a-f. Treatment of 2b with 5(3)-aminopyrazole-4-carboxylates 5a-d in the presence of NaH afforded the ethyl 6-[1,2-bis(benzyloxy)-3-hydroxypropyl]pyrazolo[1,5-a]pyrimidine-3-carboxylates 6a-d. Ring transformation of 2a,b with 2-aminobenzimidazole yielded the 3-[1,2-bis(benzyloxy)-3-hydroxypropyl]benzo[4,5]imidazo[1,2-a]pyrimidines 7a,b.

Key words

carbohydrates - heterocycles - nucleosides - ring transformation