Synlett 2009(10): 1591-1596  
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

Vadivel Vaithiyanathan, Kodirajan Selvakumar, Ponnusamy Shanmugam*
Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram 695019, Kerala, India
Fax: +91(44)24911589; e-Mail: shanmu196@rediffmail.com;
Further Information

Publication History

Received 10 October 2008
Publication Date:
02 June 2009 (online)

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.

1

Present address: Organic Chemistry Division, Central Leather Research Institute (CLRI), Adyar, Chennai 600020, India