AI Article Synopsis
- A new and efficient method using phenyliodine(III) diacetate (PIDA) has been developed to synthesize aryldiazenylisoxazolo(isothiazolo)arenes from 2-amino-N'-arylbenzohydrazides.
- The synthesis involves creating a key intermediate (E)-(2-aminoaryl)(aryldiazenyl)methanone, which then undergoes a one-pot reaction to form the final product at room temperature.
- This process differs from previous methods due to the formation of a diazo intermediate, leading to unique reactivity when reacting with carbonyl oxygen, resulting in isoxazole products.
Article Abstract
A phenyliodine(III) diacetate (PIDA)-mediated, highly efficient and tandem approach for the synthesis of aryldiazenylisoxazolo(isothiazolo)arenes from simple 2-amino-N'-arylbenzohydrazides has been developed. The reaction proceeds via formation of (E)-(2-aminoaryl)(aryldiazenyl)methanone as the key intermediate, followed by intramolecular oxidative O-N/S-N bond formation in one pot at room temperature. The quiet different reactivity of the substrate is due to the formation of a diazo intermediate which encounters a nucleophilic attack by carbonyl oxygen on the electrophilic amine to produce isoxazole products, as compared to the previous reportsa,b,4 in which an N-acylnitrenium ion intermediate is intramolecularly trapped by an amine group.
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| http://dx.doi.org/10.1021/acs.joc.5b02276 | DOI Listing |
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