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Issue 38, 2012
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DABCO and Bu3P catalyzed [4 + 2] and [3 + 2] cycloadditions of 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate

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Abstract

DABCO-catalyzed [4 + 2] and Bu3P-catalyzed [3 + 2] cycloadditions between 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate were developed for the synthesis of dihydropyran-fused and cyclopenten-fused chromen-2-ones with high regio- and stereo-selectivities, respectively. The synthetic procedures have the advantages of mild reaction conditions, convenient handling and good atom economy as well as a wide substrate scope, which make this method useful for the synthesis of potentially biologically active dihydropyran-fused and cyclopenten-fused chromen-2-ones derivatives. Possible reaction mechanisms have also been proposed on the basis of previous literature and our investigation.

Graphical abstract: DABCO and Bu3P catalyzed [4 + 2] and [3 + 2] cycloadditions of 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate

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Publication details

The article was received on 07 Jul 2012, accepted on 02 Aug 2012 and first published on 02 Aug 2012


Article type: Paper
DOI: 10.1039/C2OB26300A
Citation: Org. Biomol. Chem., 2012,10, 7739-7746
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    DABCO and Bu3P catalyzed [4 + 2] and [3 + 2] cycloadditions of 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate

    Y. Wang, Z. Yu, H. Zheng and D. Shi, Org. Biomol. Chem., 2012, 10, 7739
    DOI: 10.1039/C2OB26300A

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