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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 7
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Original Articles

Base-Dependent Cascade Synthesis of Novel Pyrano[3,2-c]coumarin Derivatives from Baylis–Hillman Bromide

, , &
Pages 1009-1021 | Received 19 Feb 2009, Published online: 04 Mar 2010
 

Abstract

5-Oxo-2,3,4,5-tetrahydropyrano[3,2-c]chromene-3-carboxylates derived from 4-hydroxycoumarin and Baylis–Hillman bromides are efficiently obtained in excellent yields within a short time. The transformation is depends on a base, which goes through SN2-SN2 nucleophilic substitution and intramolecular Michael addition. The product structures are confirmed by x-ray crystallography, and a tentative mechanism of the cascade process is presented.

ACKNOWLEDGMENT

We are grateful for the financial support from the Science and Technology Project of Zhejiang Province (No. 2008C21033).

Notes

a The reaction was carried out in refluxing acetone with 1.2 eq base.

b Refers to the isolated mixture of 3a/4a.

c Determined by 1H NMR.

d The reaction was executed at room temperature.

e No desired product but side product was isolated.

f No reaction and bromide was quantitatively recycled.

g No desired product but bromide was completely consumed.

a Isolated overall yield of the mixture of 3 and 4.

b Determined by 1H NMR.

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