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

Alexander P. Gaywood, Hamish McNab

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Pure indoxyl can be obtained in 75% yield by flash vacuum pyrolysis (FVP) of 2'-azidoacetophenone at 650 degrees 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 2methylene compound gives pyrano[3,2-b]indol-2(5H)-one (42%).

Original languageEnglish
Pages (from-to)1361-1364
Number of pages4
JournalSynthesis: Journal of Synthetic Organic Chemistry
Issue number8
Publication statusPublished - Apr 2010

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