Synthesis of azatricyclodiones & octahydro-benzo[f]isoindoles and their antimicrobial evaluation

Abstract

A series of azatricyclodiones and octahydro-benzo[f]isoindoles have been synthesized by (4 þ 2) Diels-Alder cycloaddition of maleimides with furfuryl amine. Reaction of azatricyclodiones with isocyanates led to the respective ureides. All of the compounds were screened against a number of bacteria and fungi. One of the compounds (2) displayed moderate antitubercular activity while two compounds (2) and (4) inhibited the fungal growth at 25 mg/mL.

Comment on “An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using a zebrafish embryo model” by C. E. Puerto Galvis and V. V. Kouznetsov, Org. Biomol. Chem., 2013, 11, 407

“…Depending on the nature of the substituents on the maleimide core and the reaction conditions, the reaction could furnish different adducts. [4][5][6] For example, Saxena et al 4 reported that the reaction of N-phenyl maleimides with one equivalent of furfuryl amine in benzene at 80°C led to the formation of cycloadducts 4 via path A (Scheme 1). Moreover, the synthesis of cycloadducts 4 through a reaction of maleimides and N-acetylfurfurylamine was described in the work being criticized.…”