Vol 59, No 12 (2023)

The symposium on the chemistry of alkynes, allenes and small cycles was held from July 3 to July 6, 2023 at St. Petersburg State University as part of the All-Russian conference with international participation “Ideas and legacy of A.E. Favorsky in organic chemistry”. Leading experts in the chemistry of alkynes, allenes and small cycles took part in the symposium; the latest achievements in the chemistry of these classes of compounds were presented and further development prospects were discussed. This review contains brief annotations of the reports and references to the corresponding publications of the authors.

The “New Organic Functional Materials” seminar took place at St. Petersburg University as part of the All-Russian Conference featuring international participation that centered on “Ideas and Legacy of A.E. Favorsky in Organic Chemistry” from July 3-6, 2023. The seminar featured reports on organic materials possessing luminescent, photosensitizing, magnetic, conductive properties, and biological activity. The event also discussed innovative techniques for synthesizing functional organic molecules and their crystallochemical design. The review includes concise annotations of the reports and relevant references to the speakers’ works.

The hERG (human ether-à-go-go-related gene) potassium channel has elicited intense scientific interest due to its counter-intuitive kinetics and its association with arrhythmia and sudden death. Kv1.5 potassium channel, encoded by KCNA5, is a promising target for the treatment of atrial fibrillation, one of the common arrhythmia. A new indole derivatives were synthesized via reaction of indole-3-carboxylic acid with 4-[2-(diethylamino)ethoxy]aniline under peptide coupling protocol in DMF with good yields and evaluated their antiarrythmic activity. Among them, 2-butyl- N -{4-[2-(diethylamino)ethoxy]phenyl}-1-(2-fluorobenzoyl)-1 H -indole-3-carboxamide 34 showed preferable anti-arrhythmic effects and favoured safety. These results indicate that lead compound can be a promising antiarrythmic drug for further studies.

Optimization of the conditions of the Chan-Lam reaction was carried out to obtain N -aryl derivatives of adamantane-containing amines. Under optimal conditions [2 equiv p -tolylboronic acid, 2 equiv. DBU, 0.1 M solution in MeCN, 20 mol % Cu(OAc)₂·H₂O, 25°C, 24 h] reactions with a series of adamantane-containing amines and diamines, differing by the steric hindrances at the amino group, were performed. Strong dependence of the amine reactivity on their structure was observed, the best yield of the monoamine derivatives reached 74% and that of diamines - 66%.

The interaction of pulegone with enophil - 4-phenyl-4 H -1,2,4-triazoline-3,5-dione leads to the formation of two described earlier epimers: 1-[(1 R ,4 R )-4-methyl-1-(1-methylethenyl)-2-oxocyclohexyl]-4-phenyl-1,2,4-triazolidine-3,5-dione ( RR -isomer) and 1-[(1 S ,4 R )-4-methyl-1-(1-methylethenyl)-2-oxocyclohexyl]-4-phenyl-1,2,4-triazolidine-3,5-dione ( SR -isomer). Along with these epimers, we found another isomer - 1-{1-methyl-1-[(4 R )-4methyl-6-oxocyclohex-1-en-1-yl]ethyl}-4-phenyl-1,2,4-triazolidine-3,5-dione. Quantum chemical modeling has established that isomeric products of hydrogen substitution in pulegone by enophil are formed along three routes. In the SR -isomer formation route, the ene reaction proceeds consistently. The other two routes are implemented with the enophil approach from the R -side of the pulegon. These routes consist of two consecutive stages. At the first stage, an intermediate of the type of asymmetric cyclic aziridine cation is formed. Elimination of a proton from one of the geminal methyl groups of the intermediate leads to an RR -isomer with a terminal double bond. When a proton is eliminated from the methylene group of the pulegog ring, an internal unsaturated compound is formed. The ratio of the yield of the isomer with an internal double binding and the RR -isomer depends on the polarity of the aprotic solvents.