The Reactivity of Azidonitrobenzofuroxans towards 1,3-Dicarbonyl Compounds: Unexpected Formation of Amino Derivative via the Regitz Diazo Transfer and Tautomerism Study

Abstract

Herein, we report on the reaction of nitro-substituted azidobenzofuroxans with 1,3-dicarbonyl compounds in basic media. The known reactions of benzofuroxans and azidofuroxans with 1,3-dicarbonyl compounds in the presence of bases are the 1,3-dipolar cycloaddition and the Beirut reaction. In contrast with this, azidonitrobenzofuroxan reacts with 1,3-carbonyl compounds through Regitz diazo transfer, which is the first example of this type of reaction for furoxan derivatives. This difference is seemingly due to the strong electron-withdrawing effect of the superelectrophilic azidonitrobenzofuroxan, which serves as the azido transfer agent rather than 1,3-dipole in this case.

Bioactive Oxadiazoles 2.0

“…Additionally, benzofuroxans were presented in this issue due to their peculiar reactivity and applications. In fact, azidonitrobenzofuroxans were shown to react with 1,3-carbonyl compounds through Regitz diazo transfer [ 8 ], while benzofuroxans linked to an aminothiazole scaffold were evaluated for their anticancer activity [ 9 ].…”