Synthesis of 8-substituted bicyclo[3.2.1]octane-6-carboxylic acids and anti-convulsant properties of the corresponding amides

Synthesis of Halogenated Cyclic Enamines from Cyclic N‐2‐En‐4‐ynyl‐N‐1‐ynylamides and N‐Propargyl‐N‐1‐ynylamides via a Tandem Iron Halide Promoted N‐to‐C Shift‐Aza‐Prins Cyclization Sequence

“…Miller reported the formation of 8-chlorobicyclo[3.2.1]oct-6-ene derivatives by zinc chloride catalyzed [3 + 2] cycloaddition of cyclic allylic chlorides to alkynes. [10] It must be noted that the stabilization by the conjugated p systems of the phenylalkyne at C3 of the six-membered ring was critical since the substrate with a simple methyl group at C3 did not undergo the N-to-C allyl shift reaction path. [11] To further prove the proposed intermolecular Nto-C allyl shift, a crossover experiment in which an equimolar mixture of ynamides 1 l and 1 q was subjected to the optimal reaction conditions and the ratio of the products was examined by NMR spectroscopy (Scheme 3).…”

“…Subsequently, detachment of the iron-ketenimine moiety generates the stable allylic carbonium ion 6. [10] It must be noted that the stabilization by the conjugated p systems of the phenylalkyne at C3 of the six-membered ring was critical since the substrate with a simple methyl group at C3 did not undergo the N-to-C allyl shift reaction path. However, an alternative mechanism can also be considered (path b).…”

Acetyl- and butyrylcholinesterase inhibitory activity of selected photochemicallysynthesized polycycles

“…It is present in diterpene families of compounds, such as the kaurenes and the gibberellins, and also in many sesquiterpenes [13]. One of the more interesting properties of the bicyclo[3.2.1]octane skeleton is its rigidity, which promotes specific coordination of two or more ligands on it, which can be of great value to medicinal chemists in the search for biological activity [14][15][16][17]. This structural moiety forms a basic framework of numerous biologically active natural compounds and their metabolites [18][19][20].…”

“…Antioxidant properties of these compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) were investigated as a part of this study but were proven to be negligible and hence will not be discussed in great detail. The table with the results is given in the Supporting material (Table S1).…”

“…Absorbance measurements were performed using a Synergy HTX S1LFA multimode microplate reader (BioTek Instruments, Inc., Winooski, VT, USA). All the tested polycyclic derivatives, (11 S) -11-(4-chlorophenyl)tricyclo[6.3.1.0 2,7 ]dodeca-2,4,6,9-tetraene (1), 3-[(9 S) -tricyclo[6.3.1.0 2,7 ]dodeca-2,4,6,10-tetraen-9-yl]pyridine (2), 4-[(9 S) -tricyclo[6.3.1.0 2,7 ]dodeca-2,4,6, 10-tetraen-9-yl]pyridine (3), 3-[(9S)-tricyclo[6.3.1.0 2,7 ]dodeca-2(7),3,5,10-tetraen-9-yl]thiophene (4), (11 S)-11-(4-methoxyphenyl)-12-[(E)-2-(4-methoxyphenyl)ethenyl]tricyclo[6.3.1.0 2,7 ]dodeca-2,4,6,9-tetraene (5), (11 S) -11-(4-chlorophenyl)-12-[(E) -2-(4-chlorophenyl)ethenyl]tricyclo[6.3.1.0 2,7 ]dodeca-2,4,6,9-tetraene (6), 3-oxatetracyc-lo[6.6.1.0 2,6 .0 9,14 ]pentadeca-2(6),4,9(14),10,12-pentaen-4-ol (7), 3-oxatetracyclo[6.6.1.0 2,6 .0 9,14 ]pentadeca-2(6),4,9(14),10,12-pentaene-7-peroxol (8), 2-hydroxy-3-thiatetracyclo[6.6.1.0 2,6 .0 9,14 ]pentadeca-5,9(14),10,12tetraen-4-one (9), 5-thiatetracyclo[6.6.1.0 2,6 .09,14 ]pentadeca-2(6),3,9(14),10,12-pentaene (10), (2 S)-3-oxa-5azatetracyclo[6.6.1.0 2,6 .0 9,14 ]pentadeca-4,6,9,11,13-pentaene (11), 2-[(10 S)-tetracyclo[7.2.1.0 2,11 .0 3,8 ]dodeca-3(8),4,6-trien-10-yl]thiophene (12), 4-[(10 S)-tetracyclo[7.2.1.0 2,11 .0 3,8 ]dodeca-3,5,7-trien-10-yl]pyridine (13), and (9 S) -10-oxotricyclo[6.3.1.0 2,7 ]dodeca-2,4,6-trien-9-yl formate (14), were prepared as described previously[35,[41][42][43]45].…”