Science and Technology Production
Article
Authorship
Lucena Valentin
;
Szajnman Sergio
;
Juan B. Rodriguez
;
BONESI, SERGIO MAURICIO
Date
2024
Publishing House and Editing Place
WILEY-V C H VERLAG GMBH
Magazine
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
WILEY-V C H VERLAG GMBH
Summary
Information provided by the agent in
SIGEVA
A multi-step sequence leads to the preparation of a series of aryl selenocyanate WC-9 homologues which are interesting compounds with potential biological activity against Trypanosoma cruzi, the etiological agent of Chagas disease. The synthetic sequence involves the application of the photo-Fries rearrangement reaction as a key step for the preparation of a series of 2-hydroxyphenones bearing alkyl chains of different length and a phenyl group. These intermediates are obtained upon direct irra...
A multi-step sequence leads to the preparation of a series of aryl selenocyanate WC-9 homologues which are interesting compounds with potential biological activity against Trypanosoma cruzi, the etiological agent of Chagas disease. The synthetic sequence involves the application of the photo-Fries rearrangement reaction as a key step for the preparation of a series of 2-hydroxyphenones bearing alkyl chains of different length and a phenyl group. These intermediates are obtained upon direct irradiation (254 nm) of 4-phenoxyphenyl esters in different solvents at room temperature. Then, reaction of the 2-hydroxyphenones with 2-(2-bromoethoxy)tetrahydro-2H-pyran followed by acid deprotection, tosylation (or mesylation) reaction and, finally, nucleophilic attack with potassium selenocyanate provides the target aryloxyethyl selenocyanate homologues in good yields
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Key Words
Antiprotozoal agentaryl selenocyanatePhoto-Fries rearrangementGrowth inhibitors