Mild Synthesis of Symmetric 3,5-Disubstituted Nitrobenzenes


A mild synthesis of 3,5-disubstituted nitrobenzenes from readily available 3-formylchromones is reported. The developed methodology follows a cascade process, promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene. The proposed mechanism involves an initial Michael addition of nitromethane at C-2 of a 3-formylchromone. The resultant intermediate undergoes another Michael reaction with a second 3-formylchromone molecule. After ring closure through intramolecular cyclization, the aromatization is completed by deformylation, affording the 3,5-disubstituted nitrobenzenes in 52-86% yield. The reported method produces three new C-C bonds in a simple and straightforward manner, and it is consistent with gram-scale synthesis.






Francisco, TN; Sousa, JLC; Guieu, S; Silva, AMS; Albuquerque, HMT

nossos autores


This work was financed by Portugal 2020 through FEDER in the framework of POCI and in the scope of the projects EpigenGlicON (POCI-01-0145-FEDER-029767), LAQV-REQUIMTE (UIDB/50006/2020), and CICECO -Aveiro Institute of Materials (UIDB/50011/2020 & UIDP/50011/2020), co-financed by FCT/MCTES. J.S., H.A., and T.F. acknowledge the EpigenGlicON project (POCI-01-0145-FEDER029767) for their researcher contracts and research grant, respectively.

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