2019
DOI: 10.1002/jhet.3671
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Functionalized Benzofurans via Microwave‐Promoted Tandem Claisen‐Rearrangement/5‐endo‐dig Cyclization

Abstract: Ortho‐allyloxy alkinyl benzenes undergo, upon microwave irradiation in dimethylformamide, a tandem sequence of Claisen‐rearrangement and 5‐endo‐dig cyclization to furnish 7‐allyl‐substituted benzofurans. With terminal alkynes, chroman‐4‐ones and enaminoketones become the main products. A mechanistic proposal for this observation relies on a reaction of the starting material with the solvent dimethylformamide under the microwave conditions.

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Cited by 4 publications
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“…Microwave promoted approach towards the preparation of 7-allylsubstituted benzofurans from ortho-allyloxyalkenyl benzenes was established (Scheme 19). 53 The reaction was described to proceed via Claisen-rearrangement, followed by 5-endo-dig-cyclization forming OMe…”
Section: Scheme 18 Synthesis Of 23-disubstituted Benzo[b]furansmentioning
confidence: 99%
“…Microwave promoted approach towards the preparation of 7-allylsubstituted benzofurans from ortho-allyloxyalkenyl benzenes was established (Scheme 19). 53 The reaction was described to proceed via Claisen-rearrangement, followed by 5-endo-dig-cyclization forming OMe…”
Section: Scheme 18 Synthesis Of 23-disubstituted Benzo[b]furansmentioning
confidence: 99%