Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins

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Three-component coupling reactions of arynes for the synthesis of benzofurans and coumarins.

The domino three-component coupling reaction of arynes with DMF and active methylenes or methines was studied as a highly efficient method for preparing heterocycles. Coumarin derivative 5 was formed when diethyl malonate (2) or α-bromomalonate (3) were used as a C2-unit. In contrast, dihydrobenzofurans 7a and 7b were obtained by using α-chloroenolates generated from α-chloromalonates 4a and 4b...

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Three-component coupling using arynes and DMF: straightforward access to coumarins via ortho-quinone methides.

ortho-Quinone methides, arising from a formal [2+2] cycloaddition between arynes and DMF, were found to facilely undergo a [4+2] cycloaddition with ester enolates or ketenimine anions to produce diverse coumarins in a straightforward manner.

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Silica Sodium Carbonate as an Effective and Reusable Catalyst for the Three-Component Synthesis of Pyrano Coumarins

Silica sodium carbonate (SSC) has been used as a valuable silica-supported catalyst for the preparation of a range of known and novel pyrano coumarins via the three-component reactions of aryl aldehydes, active methylene compound (malononitrile or ethyl cyanoacetate), and hydroxycoumarin (5,7-dihydroxy-4-substituted coumarins or 4-hydroxycoumarin). The heterogeneous catalyst showed much the sam...

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ژورنال

عنوان ژورنال: Molecules

سال: 2014

ISSN: 1420-3049

DOI: 10.3390/molecules19010863