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

Irma Y. Flores-Larios, Lizbeth López-Garrido, Francisco J. Martínez-Martínez, Jorge González, Efrén V. García-Báez, Alejandro Cruz, Itzia I. Padilla-Martínez

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14 Scopus citations

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.

Original languageEnglish
Pages (from-to)1513-1530
Number of pages18
JournalMolecules
Volume15
Issue number3
DOIs
StatePublished - Mar 2010

Keywords

  • 6a,7,7a,8a,9,9a- hexahydro-7a,8a-dimethyl-6-oxo-6h-5,8-dioxacyclopropa[b]phenantrenes
  • Coumarins
  • Diels-Alder adducts
  • Solventless reactions

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