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Synthesis 2002(5): 0664-0668
DOI: 10.1055/s-2002-23543
PAPER
© Georg Thieme Verlag Stuttgart · New York

Ring Transformations of 2-Formylglycals with C,N-Dinucleophiles [1]

Alina Monteroa,b, Holger Feista, Manfred Michalikc, Jose Quincocesd, 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 Centro de Bioactivos Químicos, Universidad Central de Las Villas, Carretera a Camajuaní, km 5.5. Santa Clara, Cuba
c Institut für Organische Katalyseforschung, Buchbinderstraße 5-6, 18055 Rostock, Germany
d Universidade Bandeirante de Sao Paulo, Rua Maria Candida, 1813, Vila Guilherme, São Paulo, CEP: 02071-013, Brazil
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Received 30 November 2001
Publikationsdatum:
02. April 2002 (online)

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Abstract

The ring transformations of 2-formylglycals with 2-cyano-N-(4-methoxyphenyl)acetamide, 2-benzimidazolylacetonitrile, 2-nitromethylbenzimidazole yielded 5-(1,2,4-tri-O-benzyl-d-arabino/lyxo-1,2,3,4-tetrahydroxybutyl)-1,2-dihydro-1-(4-methoxyphenyl)-2-oxopyridine-3-carbonitriles (2), 2-(1,2,4-tri-O-benzyl-d-arabino/lyxo-1,2,3,4-tetrahydroxybutyl)benzo[4,5]imidazo[1,2-a]pyridine-4-carbonitriles (3) and 2-(1,2,4-tri-O-benzyl-d-lyxo-1,2,3,4-tetrahydroxybutyl)-4-nitrobenzo[4,5]imidazo[1,2-a]pyridine (4), respectively.

Key words

aldehydes - nucleosides - carbohydrates - formylglycals - push-pull alkenes

1

Presented at the XXth International Carbohydrate Symposium, Hamburg, Germany, 2000.