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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 11
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Original Articles

Efficient One-Pot Synthesis of Precursors of Some Novel Aminochromene Annulated Heterocycles via Domino Knoevenagel–hetero-Diels–Alder Reaction

, , , &
Pages 1577-1586 | Received 02 Oct 2011, Published online: 06 Mar 2013
 

Abstract

An efficient, one-pot synthetic approach to precursors of some new aminochromene/xanthene annulated heterocycles via a tetrabutylammonium hydrogen sulfate–mediated intramolecular domino Knoevenagel–hetero-Diels–Alder reaction is described. The method is general and efficient. The stereochemistry of the product was confirmed by various NMR experiments and single-crystal x-ray diffraction data.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

We sincerely express our thanks to the head, Department of Chemistry, S. P. University, for providing necessary research facilities. Two of us (S. B. T. and H. A. B.) are grateful to the University Grants Commission (UGC), New Delhi, for research fellowships under the UGC scheme of RFSMS.

Notes

a All reactions were carried out at reflux in CH3CN with 25 mol% TBA-HS.

b Isolated yield.

c Uncorrected.

d Product decomposed.

a All reactions were carried out at reflux in xylene with 25 mol% TBA-HS.

b Uncorrected.

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