Thermal [4 + 2] cycloadditions of 3-acetyl-, 3-carbamoyl-, and 3-ethoxycarbonyl-coumarins with 2,3-dimethyl-1,3-butadiene under solventless conditions: a structural study

The thermal [4+2] cycloadditions of 3-acetyl-, 3-carbamoyl, and 3-ethoxycarbonylcoumarins with 2,3-dimethyl-1,3-butadiene under solvent free conditions are reported, as well as the epoxidation reactions of some adducts. Discussion is focused on the structural features of the Diels-Alder adducts and...

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Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 2010-03, Vol.15 (3), p.1513-1530
Hauptverfasser:	Flores-Larios, Irma Y, López-Garrido, Lizbeth, Martínez-Martínez, Francisco J, González, Jorge, García-Báez, Efrén V, Cruz, Alejandro, Padilla-Martínez, Itzia I
Format:	Artikel
Sprache:	eng
Schlagworte:	6a,7,7a,8a,9,9ahexahydro-7a,8a-dimethyl-6-oxo-6H-5,8-dioxacyclopropa[b]phenantrenes Alkenes - chemistry Butanes - chemistry coumarins Coumarins - chemistry Cyclization Diels-Alder adducts Magnetic Resonance Spectroscopy Mass Spectrometry Models, Molecular Molecular Structure solventless reactions Solvents Temperature
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Zusammenfassung:	The thermal [4+2] cycloadditions of 3-acetyl-, 3-carbamoyl, and 3-ethoxycarbonylcoumarins with 2,3-dimethyl-1,3-butadiene under solvent free conditions are reported, as well as the epoxidation reactions of some adducts. Discussion is focused on the structural features of the Diels-Alder adducts and their epoxides, based upon NMR, X-ray, and mass spectral data, and supported by ab initio theoretical calculations.
ISSN:	1420-3049 1420-3049
DOI:	10.3390/molecules15031513