Sequential one-pot method for oxy-Michael addition, Heck coupling, and degradation followed by condensation: facile synthesis of 2-benzoxepin-3(1H)-ones

A sequential one-pot intermolecular oxy-Michael addition, intermolecular Heck coupling, and intramolecular degradation (retro-oxy-Michael addition) followed by condensation method has been developed for the synthesis of interesting 2-benzoxepin-3(1H)-ones. Significantly, the 2-benzoxepin-3(1H)-ones...

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Bibliographic Details
Published in:Tetrahedron 2013-11, Vol.69 (47), p.10098-10107
Main Authors: Reddy, A. Gopi Krishna, Krishna, J., Satyanarayana, G.
Format: Article
Language:English
Subjects:
2-Benzoxepin-3(1H)-ones
Carbon-carbon composites
Condensates
Condensation
Degradation
Heck coupling
Isomerization
Joining
Michael reaction
Oxy-Michael addition
Pd-catalysis
retro-Oxy-Michael addition
Solvent effect
Synthesis
Tetrahedrons
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Summary:A sequential one-pot intermolecular oxy-Michael addition, intermolecular Heck coupling, and intramolecular degradation (retro-oxy-Michael addition) followed by condensation method has been developed for the synthesis of interesting 2-benzoxepin-3(1H)-ones. Significantly, the 2-benzoxepin-3(1H)-ones form the core quantum of biologically vital natural products. The initial oxy-Michael addition and Heck coupling steps involve a straight forward construction of C–O and C–C bonds, whereas, the final condensation step follows a novel mechanistic path via intramolecular degradation, double bond isomerization, and intramolecular condensation. Notably, a remarkable solvent effect has been observed in-order to promote the final intramolecular condensation. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.09.050