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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 22
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Original Articles

Efficient Route to Highly Functionalized Chalcone-Based Pyranocoumarins via Iodine-Promoted Michael Addition Followed by Cyclization of 4-Hydroxycoumarins

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Pages 3044-3053 | Received 10 Oct 2012, Published online: 08 Aug 2013
 

Abstract

Molecular iodine is used as an efficient promoter in the regioselective synthesis of highly functionalized chalcone-based pyranocoumarin derivatives using 4-hydroxycoumarin in acetic acid solvent at 100 °C. Under optimized reaction conditions, our protocol (Michael addition followed by intermolecular cyclization) has tolerance for many functional groups and gave products in good to excellent yields (75–98%) within 1–2 h.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource: Full experimental and spectral details.]

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

We thank the Department of Science and Technology, New Delhi, for financial support and the Department of Chemistry, Indian Institute of Technology Roorkee for the Ministry of Human Resource Development fellowship to B. V. B.

Notes

Note. MgO, ZnO, CuO, LaCl3, BiNO3, SnCl4, SnCl2·2H2O, TaCl5, LaCl3, CuBr2, and TiCl4: no product obtained.

a Isolated yield.

b No reaction (NR).

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