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    Diversity-Oriented Synthesis of Privileged Benzopyranyl Heterocycles from s-cis-Enones
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    Department of Chemistry, Seoul National University, Seoul, 151-747, Korea, and Bioinformatics & Molecular Design Research Center, Seoul, 120-749, Korea
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2008, 73, 5, 1752–1761
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    https://doi.org/10.1021/jo702196f
    Published February 12, 2008
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    Abstract

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    A novel strategy for the construction of benzopyranyl heterocyclic series with maximized diversity in the polar surface area on rigid scaffolds has been developed through a divergent synthetic pathway with high efficiency. s-cis-Enones embedded in a benzopyran skeleton were identified as versatile key intermediates for the synthesis of four different heterocycle libraries fused with a benzopyran substructure. These four novel core skeletons were designed by a creative recombination of the privileged skeletons:  benzopyran, pyridine, pyrazole, pyrazolopyrimidine, and pyrimidine. The regioselective synthesis of each core skeleton was achieved by the introduction of three s-cis enone intermediates. This paper also explores the regioselective formation of arylpyrazole through the condensation of β-keto aldehyde with arylhydrazine under three different conditions and presents the mechanistic information that was obtained from the regioisomeric ratio of arylpyrazole based on the substituent's electronic effect and reaction temperature. It appears that the regioselective synthesis of arylpyrazole was achieved through the intriguing interplay of the nucleophilicity on arylhydrazine and the electrophilicity on dielectrophiles.

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     Seoul National University.

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     Bioinformatics & Molecular Design Research Center.

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    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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    General experimental procedures, structural confirmation of each core skeleton (I−IV), as well as 1H NMR and 13C NMR spectra and mass spectra for all new compounds. Crude 1H NMR spectra for typical patterns of regioisomers in pyrazole synthesis. Data from computational studies including principle component analysis loading data, conformer alignment, and isosurface diagrams. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Org. Chem. 2008, 73, 5, 1752–1761
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    https://doi.org/10.1021/jo702196f
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