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Molecules 2010, 15(3), 1513-1530; doi:10.3390/molecules15031513
Article

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

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Received: 4 December 2009; in revised form: 27 February 2010 / Accepted: 8 March 2010 / Published: 9 March 2010
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Abstract: 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.
Keywords: coumarins; Diels-Alder adducts; solventless reactions; 6a,7,7a,8a,9,9ahexahydro-7a,8a-dimethyl-6-oxo-6H-5,8-dioxacyclopropa[b]phenantrenes coumarins; Diels-Alder adducts; solventless reactions; 6a,7,7a,8a,9,9ahexahydro-7a,8a-dimethyl-6-oxo-6H-5,8-dioxacyclopropa[b]phenantrenes
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Flores-Larios, I.Y.; López-Garrido, L.; Martínez-Martínez, F.J.; González, J.; García-Báez, E.V.; Cruz, A.; Padilla-Martínez, I.I. 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. Molecules 2010, 15, 1513-1530.

AMA Style

Flores-Larios IY, López-Garrido L, Martínez-Martínez FJ, González J, García-Báez EV, Cruz A, Padilla-Martínez II. 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. Molecules. 2010; 15(3):1513-1530.

Chicago/Turabian Style

Flores-Larios, Irma Y.; López-Garrido, Lizbeth; Martínez-Martínez, Francisco J.; González, Jorge; García-Báez, Efrén V.; Cruz, Alejandro; Padilla-Martínez, Itzia I. 2010. "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." Molecules 15, no. 3: 1513-1530.



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