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Synthesis 2010(8): 1361-1364  
DOI: 10.1055/s-0029-1218668
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Methylene Meldrum’s Acid Derivatives of Indoxyl and Their Cyclization Reactions under Flash Vacuum Pyrolysis Conditions

Alexander P. Gaywood, Hamish McNab*
School of Chemistry, The University of Edinburgh, West Mains Road, Edinburgh EH9 3JJ, UK
Fax: +44(131)6504743; e-Mail: H.McNab@ed.ac.uk;
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Publication History

Received 27 November 2009
Publication Date:
05 February 2010 (online)

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Abstract

Pure indoxyl can be obtained in 75% yield by flash vacuum pyrolysis (FVP) of 2′-azidoacetophenone at 650 ˚C. Reaction of indoxyl with methoxymethylene Meldrum’s acid takes place at the 1-position, and FVP of the resulting derivative provides 1-hydroxy-9H-pyrrolo[1,2-a]indol-9-one (54%). FVP of the isomeric 2-methylene compound gives pyrano[3,2-b]indol-2(5H)-one (42%).

Key words

gas-phase reactions - cyclisations - heterocycles - pyro­lysis - ketenes

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