Premium
A Synthetic Pathway to Substituted Benzofuroxans through the Intermediacy of Sulfonates: The Case Example of Fluoro‐Nitrobenzofuroxans
Author(s) -
Jovené Cyril,
Marrot Jérome,
Jasmin JeanPhilippe,
Chugunova Elena,
Goumont Régis
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600657
Subject(s) - chemistry , deoxygenation , reactivity (psychology) , combinatorial chemistry , stereochemistry , computational chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Benzofuroxans are well known compounds that continue to attract particular attention since the discovery of 4,6‐dinitrobenzofuroxan (DNBF) back in 1899. It has been shown that these compounds possess biological activities that are related to their electronic behaviours and the positioning of substituents borne by the heterocycles. In this paper, we report the first synthesis of 4‐fluoro‐6‐nitrobenzofuroxan and 6‐fluoro‐4‐nitrobenzofuroxan; the altered positions of the substituents enabling us to carry out structural and reactivity comparisons, with DNBF and 4,6‐difluorobenzofuroxan. These compounds have been unambiguously characterized through NMR and radiocrystallographic studies. Two main synthetic pathways involving fluoroanisoles and fluorophenols, cheap and easily available chemicals, have been successfully developed. Finally, benzofurazan analogues have been prepared via deoxygenation of corresponding benzofuroxans with triethylphosphite.