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Synthesis 2002(11): 1546-1552
DOI: 10.1055/s-2002-33334
PAPER
© Georg Thieme Verlag Stuttgart · New York

Eclectic 1-Aryl-1,2-diazabuta-1,3-dienes: Valuable Tools for the Preparation of Pyrrol-2-ones, 1-Arylpyrazoles, 2-(3-Oxopyrazol-4-yl)malonates and
4-(2-Oxopyrrol-3-yl)pyrazol-3-ones

Orazio A. Attanasi, Lucia De Crescentini, Gianfranco Favi, Paolino Filippone*, Fabio Mantellini, Stefania Santeusanio
Istituto di Chimica Organica, Università di Urbino, Piazza della Repubblica 13, 61029 Urbino, Italy
Fax: +39(722)2907; e-Mail: attanasi@uniurb.it;
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Publication History

Received 22 March 2002
Publication Date:
23 August 2002 (online)

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Abstract

1-Aryl-1,2-diazabuta-1,3-dienes react with dimethyl malonate to give hydrazonic intermediates that in turn are converted into pyrrol-2-ones, 1-arylpyrazoles and 2-(3-oxopyrazol-4-yl)malonates. The latter compounds represent an useful entry to 4-(2-oxopyrrol-3-yl)pyrazol-3-ones, by means of the addition of another molecule of 1,2-diazabuta-1,3-diene and subsequent cyclization of the adducts.

Key words

1,2-diazabuta-1,3-dienes - Michael additions - cyclizations - pyrroles - pyrazoles

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