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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

1, 2, 1,* , 1, 2, 2 and 2,*
1 Facultad de Ciencias Químicas, Universidad de Colima, km 9 Carretera Coquimatlán-Colima, Coquimatlán Colima 28400, Mexico 2 Departamento de Química, Unidad Profesional Interdisciplinaria de Biotecnología del Instituto Politécnico Nacional, Av. Acueducto s/n, Barrio la Laguna Ticomán 07340, México D. F., Mexico
* Authors to whom correspondence should be addressed.
Received: 4 December 2009 / Revised: 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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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.

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