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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 (CC BY 3.0).
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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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