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Synthesis 2001(12): 1837-1845
DOI: 10.1055/s-2001-17510
PAPER
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of Stable 2-(Trifluoromethyl)-2,3-dihydro-1H-pyrrol-2-ols and Derived Fluorinated Heterocycles

Orazio A. Attanasi, Paolino Filippone*, Barbara Guidi, Fabio Mantellini, Stefania Santeusanio*
Organic Chemistry Institute, University of Urbino, Piazza della Repubblica 13, 61029 Urbino, Italy
Fax: +39(0722)2907; e-Mail: attanasi@uniurb.it;
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Publication History

Received 14 May 2001
Publication Date:
11 August 2004 (online)

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Abstract

1,2-Diaza-1,3-butadienes react regioselectively with trifluoromethylated β-dicarbonyl compounds to give stable 2-(trifluoromethyl)-2,3-dihydro-1H-pyrrol-2-ol derivatives, which upon treatment with trifluoromethanesulphonic anhydride or with heterogeneous catalysts give rise to fluorinated 1-aminopyrrole derivatives in good to excellent yields. The reaction of 2-(trifluoromethyl)-2,3-dihydro-1H-pyrrol-2-ol derivative with 2-haloketone affords fluorinated furo[2,3-b]pyrroline derivative, while that of diethyl 1-[(anilinocarbonyl)amino]-2-methyl-5-(trifluoromethyl)-1H-pyrrole-3,4-dicarboxylate with hydrazine hydrate affords fluorinated pyrrolo[3,4-d]pyridazindione derivative.

Key words

1,2-diaza-1,3-butadienes - Michael additions - regioselectivity - 2-(trifluoromethyl)-2,3-dihydro-1H-pyrrol-2-ols - heterocycles

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