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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 20
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Original Articles

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

, &
Pages 3657-3665 | Received 22 Mar 2007, Published online: 05 Oct 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.

Acknowledgment

We thank the Council of Scientific and Industrial Research (CSIR) (New Delhi) for financial assistance. Two of us (D. S. and P. D.) are grateful to the CSIR for senior research fellowships. We also thank the Department of Science and Technology (DST) (New Delhi) for providing UV‐vis and IR spectrometers under the DST‐Financial Assistance for Infrastructural Development of Science and Technology (FIST) Program.

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