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Synthesis 2003(14): 2138-2144
DOI: 10.1055/s-2003-41047
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Oxidative Cleavage of 1- and 2-Alkyl Derivatives of (exo,exo)-5,6-Dihydroxy-4,5,6,7-tetrahydro-4,7-methanoindazoles

Marcos Daniel Garcíaa, Olga Caamaño*a, Franco Fernándeza, María José Figueiraa, Generosa Gómezb
a Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Fax: +34(98)1594912; e-Mail: qoolga@usc.es;
b Departamento de Química Orgánica, Facultade de Ciencias, Lagoas-Marcosende, Universidade de Vigo, 36200 Vigo, Spain
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Publication History

Received 20 June 2003
Publication Date:
22 August 2003 (online)

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Abstract

Reaction of hydrazine with exo,exo-3-hydroxymethylene-5,6-isopropylidenedioxybicyclo[2.2.1]heptan-2-one led to norbornenepyrazole 7, which was converted to its 1- and 2-alkyl derivatives. Deprotection of the vicinal hydroxyls, oxidative cleavage of the resulting glycol and reduction of the dialdehyde so obtained afforded 1- and 2-alkylcyclopenta[c]pyrazole-4,6-dimeth-anols, which are of interest as intermediates in the preparation of nucleoside analogues derived from 1H- and 2H-cyclopenta[c]pyrazole.

Key words

indazoles - pyrazoles - heterocycles - alkylations - cleavage - nucleosides

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The crystallographic data of 12 and 15 have been deposited at the Cambridge Crystallographic Data Centre as Supplementary Publications, CCDC 189028 and CCDC 189029, respectively. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK.