An expedient route to indoles via a cycloaddition/cyclization sequence from (Z)-1-methoxybut-1-en-3-yne and 2H-pyran-2-ones |
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Authors: | Krištof Kranjc |
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Institution: | Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ašker?eva 5, SI-1000 Ljubljana, Slovenia |
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Abstract: | The cycloaddition of (Z)-1-methoxybut-1-en-3-yne (2) with 5,6-disubstituted 3-acylamino-2H-pyran-2-ones 1 under microwave-irradiation conditions, with classical heating or at high-pressures (13-15 kbar) affords the benzene derivatives 3 with a strategically positioned 2-methoxyethenyl moiety. In some cases, at high-pressures after long reaction times, 2,2-dimethoxyethyl products 4 were obtained. Adducts 3 and 4 can be cyclized under mild conditions into 1,5,6-trisubstituted indole derivatives 5. |
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