Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction
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American Chemical Society
Abstract
The discovery of a new variation on the Davis-Beirut reaction is described in which an atypical heterocyclic framework (the anthranil or benzo[c]isoxazole framework) is formed as the result of diversion of a key reactive intermediate away from its expected reactivity - a potentially general approach to reaction design and development. Experimental and computational support for the proposed mechanism and origins of altered reactivity are described. © 2017 American Chemical Society.
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Keywords
Isoxazoles, Molecular structure, Quantum theory, Organic compounds, Anthranilic acid derivative, Heterocyclic compound, Isoxazole derivative, Nitrobenzene derivative, Anthranil, Design and development, Organic chemistry, Reactive intermediate, Article, Chemical reaction, Crystal structure, Davis beirut reaction, Photochemistry, Quantum yield, Reaction analysis, Tautomerization, X ray crystallography, Chemical structure, Chemistry, Synthesis, Reaction intermediates