Synthesis of novel indenoquinolines and indenopyridazines via photoisomerization of benzotropolone derivatives

Preparation of Substituted Dihydrofluorenones by Photoisomerization of Benzotropolone Derivatives

“…Indenoquinolines and indenopyridazines obtained by photoisomerization of oxazines and hydrazines. [7] PHOTOISOMERIZATION OF BENZOTROPOLONE DERIVATIVES 2853…”

“…[3,5] We recently reported that these compounds can be transformed into novel indenoquinolines and indenopyridazines by means of photoisomerization reactions (Fig. 1), [7] an approach that could provide a convenient and simple route to expand the structural diversity of our current lead libraries. The study also revealed that despite having similar frameworks and bearing identical b,c-unsaturated ketone chromophores, [8] the outcome of the photoisomerization depends on the nature of the heteroatomic fragment.…”

Mechanistic Studies of the Formation of Functionalized Cyclopropanes through Photoisomerization of Tropolone Diels-Alder Adducts

“…[1][2][3][4][5] Some of these compounds display promising in vitro activities against Trypanosoma cruzi and Leishmania donovani. To expand the structural diversity of our libraries, and based on results obtained for similar β,γ-unsaturated ketone chromophores, 7,8 we studied the photoisomerization these alkyltropolone derivatives. As detailed herein, irradiation of these compounds leads to functionalized cyclopropanes in good yields.…”

Photochemical Preparation of Novel Tetracyclic Indenoquinolines from Benzotropolone Derivatives

“…1,2 We have shown that a novel class of tetracyclic tetraindenoquinolines could be obtained through photoisomerization of benzotropolone derivatives. 3 In this presentation we detail the preparation of a series of these compounds as well as the corresponding indenoquinolines ( Figure 1), and discuss their biological evaluation.…”