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Full Paper
Furo[3,4-b]benzodioxin Cycloadditions – A One-Pot Synthesis of Functionalized Bis-Adducts
Article first published online: 12 MAR 2009
DOI: 10.1002/ejoc.200800967
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Bozzo, C., Mur, N., Constans, P. and Pujol, M. D. (2009), Furo[3,4-b]benzodioxin Cycloadditions – A One-Pot Synthesis of Functionalized Bis-Adducts. European Journal of Organic Chemistry, 2009: 2174–2178. doi: 10.1002/ejoc.200800967
Publication History
- Issue published online: 15 APR 2009
- Article first published online: 12 MAR 2009
- Manuscript Received: 2 OCT 2008
Funded by
- Spanish Ministerio de Educación y Ciencia. Grant Number: CTQ2007-60614/BQU
- University of Barcelone, Spain. Grant Number: ACES, 2006-07
- Departament de la Generalitat de Catalunya, Spain. Grant Number: 2005-SGR-00180
Keywords:
- Cycloaddition;
- Fused-ring systems;
- Polycycles;
- Dienophiles;
- Oxygen heterocycles
Graphical Abstract
Furo[3,4-b]benzodioxin 1 reacts with a suitable dienophile to give a mono-adduct that proves the first reaction transforms the C4a–C10a bond into a double bond. Subsequently, the internal double bond of the 1,4-benzodioxin framework acts a new dienophile in a second cycloaddition reaction. With this uninterrupted cycloaddition sequence, the formation of stable bis-adducts was observed.
Abstract
Furo[3,4-b]benzodioxin 1 was found to undergo a doubleDiels–Alder reaction with several dienophiles. The diene reacts directly with the suitable dienophile to give the mono-adduct intermediate that unexpectedly leads to a second cycloaddition at the internal, electron-rich, oxabicyclic C4a–C10a double bond. The resulting bis-adducts were formed under relatively mild conditions with dienophiles ranging from maleic anhydride and dimethyl acetylenedicarboxylate to the extremely reactive arynes. With this methodology of two uninterrupted sequential cycloaddition reactions, interesting formation of stable bis-adducts was observed. The dienophile behavior of 1,4-benzodioxin is described for the first time in this work.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)