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Synlett 2009(10): 1591-1596
DOI: 10.1055/s-0029-1217194
DOI: 10.1055/s-0029-1217194
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Highly Functionalized Allene-Appended Oxindoles and 2-Oxo-1,2-dihydroindol-3-ylidene-2,5-dihydrofurans via Claisen Rearrangement and Cyclization
Further Information
Received
10 October 2008
Publication Date:
02 June 2009 (online)
Publication History
Publication Date:
02 June 2009 (online)
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Abstract
Synthesis of highly functionalized allene appended oxindole derivatives from vinyl propargyl ether derivatives of Morita-Baylis-Hillman adducts of isatin via Claisen rearrangement has been achieved. Synthetic utility of the allene derivatives obtained has been demonstrated with the synthesis of methyl 2,5-dihydro-5-methyl-2-(1-methyl-2-oxoindolin-3-ylidene)furan-3-carboxylates in a one-pot cyclization reaction under basic conditions. A plausible mechanism of the reaction is presented.
Key words
Morita-Baylis-Hillman adduct - Claisen rearrangement - isatin - allenes - vinyl propargyl ethers - dihydrofuran
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References and Notes
Present address: Organic Chemistry Division, Central Leather Research Institute (CLRI), Adyar, Chennai 600020, India