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Synthesis 2011(1): 127-132  
DOI: 10.1055/s-0030-1258346
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Alternative Synthesis of 2-Alkylidene-3,4-dihydro-2H-1,4-benzoxazines by Intramolecular Gold-Catalyzed Hydroalkoxylation of 2-(Prop-2-yn-1-ylamino)phenols

Angelo M. Manzo*a, Alcide Perbonia, Gianluigi Broggini*b, Micol Rigamontib
a Chemical Development, GlaxoSmithKline Medicine Research Center, via Fleming 4, 37135 Verona, Italy
Fax: +39(045)8218117; e-Mail: angelomaria.manzo@tin.it;
b Dipartimento di Scienze Chimiche e Ambientali, Università degli Studi dell’Insubria, via Valleggio 11, 22100 Como, Italy
Fax: +39(031)2386449; e-Mail: gianluigi.broggini@uninsubria.it;
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Publication History

Received 7 October 2010
Publication Date:
01 December 2010 (online)

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Abstract

An efficient gold-catalyzed procedure to synthesize 2-alkylidene-3,4-dihydro-2H-1,4-benzoxazines has been developed starting from 2-alkynyl-substituted phenols. This is an intramolecular hydroalkoxylation reaction on alkynes tethered to a phenol moiety that represents a valuable alternative to the already reported transition-metal-catalyzed procedures.

Key words

transition metals - heterocycles - alkynes - phenols - fused-ring systems