An expedient route to indoles via a cycloaddition/cyclization sequence from (Z)-1-methoxybut-1-en-3-yne and 2H-pyran-2-ones

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 (13–15kbar) affords the benzene derivatives 3 with a strategically positioned 2-methoxyethenyl moiety. In some...

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Published in:Tetrahedron 2008-01, Vol.64 (1), p.45-52
Main Authors: Kranjc, Krištof, Kočevar, Marijan
Format: Article
Language:English
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Summary: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 (13–15kbar) 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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.10.099