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Studies on Sequential Claisen Rearrangement: Charge-Accelerated [3,3]-Sigmatropic Rearrangement Leading to Polyheterocycles.

Authors :
Majumdar, K.C.
Saha, D.
Debnath, P.
Source :
Synthetic Communications. 2007, Vol. 37 Issue 20, p3657-3665. 9p. 3 Diagrams.
Publication Year :
2007

Abstract

A number of quinolone-annulated pentacycles have been regioselectively synthesized in 90-95% yields by sequential Claisen rearrangements. The second synthesis is anhydrous AlCl3-catalyzed charge-accelerated aromatic Claisen rearrangement of 1-aryloxymethyl-6-alkyl-3H-pyrano[2,3-c]quinolin-5(6H)-ones in dichloromethane at rt for 5-10 min. The precursors were synthesized by the thermal [3,3]-sigmatropic rearrangement of the corresponding ethers. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00397911
Volume :
37
Issue :
20
Database :
Academic Search Index
Journal :
Synthetic Communications
Publication Type :
Academic Journal
Accession number :
26951872
Full Text :
https://doi.org/10.1080/00397910701557812