Facile Regioselective Synthesis of Pyrrolo-Pyrones: Tandem Reaction of 4- N-(4 -Aryloxy-2 -ynyl), N-Methyl Pyran-2-Ones with 3-Chloroperoxybenzoic Acid (Experimental Section)

Author(s): Krishna C. Majumdar, Habibur Rahaman, Brindaban Roy.

Journal Name: Letters in Organic Chemistry

Volume 2 , Issue 8 , 2005

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A number of 6-methyl-4-N-(4-aryloxybut-2-ynyl)-N-methylaminopyran-2-ones (3a-g) on treatment with one equivalent of 3-chloroperoxybenzoic acid at 0-5 C during 25 minutes and then stirring at room temperature for 9 h afforded pyrrolo[3,2-c]pyrone derivatives (4a-g) in (80-85 %) yield. 6-Methyl-4-N-(4- aryloxybut-2-ynyl)N-methylaminopyran-2-ones (3a-g) were in turn prepared from 4-tosyloxy-6-methylpyran- 2-ones (1) and N-(4-aryloxybut-2-ynyl)- N-methylamine (2a-g).

Keywords: Amine-oxide rearrangement, [2,3]-sigmatropic rearrangement, pyrrolo-pyrone, heterocycles, N-(4-aryloxybut-2-ynyl)-N-methylamine, m-Chloroperoxybenzoic acid

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Article Details

Year: 2005
Page: [739 - 741]
Pages: 3
DOI: 10.2174/157017805774717580
Price: $65

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