Photochemical Approach to New Polycyclic Substrates Suitable for Further Photocatalytic Functionalization

Functionalization of the benzobicyclo[3.2.1] octadiene skeleton possessing one isolated double bond via photocatalytic oxygenation

“…The new products 2-7 were isolated and completely characterized by spectroscopic methods. From the 1 H and 13 C NMR spectra and taking as reference the previous results for starting compounds 1a-c, [12][13][14] the structures of all the compounds were determined. All the photoproducts have recognizable patterns in their 1 H NMR spectra ( Figure 1-5) but different numbers of signals in their aliphatic regions, depending on the structure.…”

“…12,13,14 Three phenyl derivates, 9-phenyl-, 9-(4-chlorophenyl-, and 9-(4-methoxyphenyl)-tricyclo[6.3.1.0 2 , 7 ]dodeca-2,4,6,10-tetraene (1a, 1b, and 1c, respectively) have been involved in our study: without any substituent (1a), containing a chloro (1b) or a methoxy substituent (1c) in para position. Similarly to our earlier experiments, both anionic and cationic manganese(III) porphyrins Mn (III)TSPP 3-and Mn(III)TMPyP 5+ , where H2TSPP 4-= 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin and H2TMPyP 4+ = 5,10,15,20-tetrakis(1-methyl-4-pyridinium)porphyrin) were applied in order to study the charge effect, beside the influence of the substituent on the phenyl ring.…”

A simple and easy to perform synthetic route to functionalized thienyl bicyclo[3.2.1]octadienes

“…The bicyclo [3.2.1]octane skeleton has become the subject of intensive research in recent years [1][2][3]. Its presence in numerous biologically active natural compounds ( Figure 1) [4][5][6][7], their strenuous isolation procedures from plants, as well as their complicated multistage synthesis due to the complexity of their structure, encouraged us to develop a simple one-step synthetic procedure based on a photochemical methodology [8][9][10][11][12][13][14][15][16][17][18][19][20][21]. By using a simple photochemical procedure, it was possible to obtain a whole library of novel bicyclo[3.2.1]octadiene derivatives, available for further functionalization, which could enable the easier investigation of the relationship between structure and biological activity.…”

Acetyl- and butyrylcholinesterase inhibitory activity of selected photochemicallysynthesized polycycles

“…Various syntheses of compounds containing bicyclo[3.2.1]octane/octene/octadiene cores are documented in the literature [23][24][25][26][27]. The benzobicyclo[3.2.1]octadiene skeleton can be constructed using different synthetic pathways, one of which is the photochemical approach that has been developed by our group in batch photochemical reactors [28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45]. Photochemically induced organic reactions provide an important and easy path to complex products from simple starting materials.…”