Chemistry of Heterocyclic Compounds

Saliyeva, Lesya M.; Dyachenko, Irina V.; Danyliuk, Ivanna Yu.; Vovk, Mykhailo V.

doi: 10.1007/s10593-023-03142-wpmid: 36687505

[graphic not available: see fulltext]The review summarizes and systematizes the literature data on the synthesis and some aspects of application of pyrrolo[1,2-a]imidazoles. Synthetic approaches are grouped according to the degree of saturation of the product pyrroloimidazole ring. The bibliography of the review includes 110 sources over the last 15 years.

Dotsenko, Victor V.; Varzieva, Ekaterina А.

doi: 10.1007/s10593-023-03143-9pmid: N/A

[graphic not available: see fulltext][graphic not available: see fulltext]The microreview summarizes the data published over the last 10 years on the methods of preparation and properties of 6-(aryldiazenyl)-4H-chromenes, a new promising class of compounds incorporating the azo and 4H-chromene fragments in their structure. The material is systematized according to the structure of the starting reagents.[graphic not available: see fulltext]

Sadykhov, Gusein A. o.; Verbitskiy, Egor V.

doi: 10.1007/s10593-023-03144-8pmid: N/A

[graphic not available: see fulltext][graphic not available: see fulltext]In this minireview, we cover new methods for the synthesis of indolo[2,3-b]quinoxaline derivatives that have been published over the previous decade. The majority of the approaches reported in the literature rely on transition-metal-catalyzed cross-coupling reactions and direct С–Н functionalization, as well as intramolecular oxidative cyclodehydrogenation processes (SNH reactions).[graphic not available: see fulltext]

Smits, Rufus; Belyakov, Sergey; Petrova, Marina; Kozhich, Vladislav; Muhamadejev, Ruslan

doi: 10.1007/s10593-023-03145-7pmid: N/A

[graphic not available: see fulltext]Trimethyl or triethyl phosphite in the Arbuzov reaction with 6-bromomethyl-3,4-dihydropyrimidin-2(1H)-one or analogous 6-bromomethyl-3,4-dihydropyridin-2(1H)-one provided the respective 6-alkylphosphonates in excellent yields. The heterocyclic alkylphosphonates are useful synthons in the Horner–Wadsworth–Emmons reaction for introducing a styryl moiety. Bromination of 6-methyl-4-phenyl-3,4-dihydropyridin-2(1H)-one with NBS in methanol resulted in an unexpected compound, while bromination in chloroform with bromine yielded the expected 6-bromomethyl-3,4-dihydropyridin-2(1H)-one, which undergoes facile nucleophilic substitutions. The intermediates and products are validated by single crystal X-ray diffraction.

Shutalev, Anatoly D.; Fesenko, Anastasia A.; Strel’tsova, Elena D.

doi: 10.1007/s10593-023-03146-6pmid: N/A

[graphic not available: see fulltext]A new general approach to a large variety of hitherto hardly accessible 4-unsubstituted and 4-alkyl-substituted 5-acyl-1,2,3,4-tetrahydropyrimidine-2-thiones(ones) has been developed. The approach is based on the reaction of enolates of various 1,3-diketones or β-oxoesters with readily available N-[alkyl(tosyl)methyl]thioureas, N-(azidomethyl)thiourea, and N-[alkyl(tosyl)methyl]ureas followed by TsOH-catalyzed dehydration of the intermediate 4-hydroxyhexahydropyrimidine-2-thiones(ones) without or with isolation of the latter.

Kozlenko, Anastasia S.; Pugachev, Artem D.; Ozhogin, Ilya V.; Tkachev, Valery V.; Bykusov, Vladislav V.; Stankevich, Natalia V.; Aldoshin, Sergei M.; Minkin, Vladimir I.; Lukyanov, Boris S.

doi: 10.1007/s10593-023-03147-5pmid:

Filimonov, Victor D.; Sanzhiev, Aldar N.; Gulyaev, Roman O.; Krasnokutskaya, Elena A.; Bondarev, Alexander A.

doi: 10.1007/s10593-023-03148-4pmid: N/A

[graphic not available: see fulltext]Herein, we report the first example of diazotization of aminopyridines and aminoquinolines with t-BuONO in hexafluoropropan-2-ol in the absence of acids or other initiators. For aminopyridines, this reaction is the first general route toward 2-, 3-, and 4-[(1,1,1,3,3,3-hexafluoropropan-2-yl)oxy]pyridines.

Glushkov, Vladimir A.; Mosheva, Kseniya A.; Zaitsev, Mark M.; Pelykh, Vera S.; Karasik, Valeriya I.; Andreev, Alexander I.; Dmitriev, Maksim V.

doi: 10.1007/s10593-023-03149-3pmid: N/A

[graphic not available: see fulltext]Cyclization of 1-hydrazinyl-3,3-dimethyl-3,4-tetrahydro-5H-benzo[c]azepine with ethyl orthoformate gave 5,5-dimethyl-6,7-dihydro-5Hbenzo[c]-1,2,4-triazolo[3,4-a]azepine, and its reaction with acetic acid afforded 3,5,5-trimethyl-9,10-dimethoxy-6,7-dihydro-5Н-benzo[c]-1,2,4-triazolo[3,4-a]azepine. Nitrosation of 1-hydrazino-3,3-dimethyl-3,4-tetrahydro-5H-benzo[c]azepine led to the formation of substituted 6,7-dihydro-5H-benzo[c]tetrazolo[5,1-a]azepines.

Lielpētere, Anna; Šilaks, Artūrs; Jirgensons, Aigars

doi: 10.1007/s10593-023-03150-wpmid: N/A

[graphic not available: see fulltext]Electrochemical activation of trialkylstannylmethyl group as an electroauxiliary for carbenium ion generation enables the intramolecular Friedel–Crafts alkylation. Electrochemical activation of stannylmethyl group forms carbenium ion which can be trapped by intramolecular (het)aromatic nucleophiles for the formation of new 6-membered cycles.

Solomin, Vitalii V.; Ciruelos, Blanca Fernandez; Velikova, Nadya; Wells, Jerry; Albanese, Marco; Adhav, Anmol; Jirgensons, Aigars

doi: 10.1007/s10593-023-03151-9pmid: N/A

[graphic not available: see fulltext]Series of new potent inhibitors of growth of Staphylococcus aureus Newman, based on 3,4-diphenylpyrazole and 4,5-diphenylisoxazole derivatives were discovered. Structures of interest were selectively modified to check their structure–activity relationship. Studies revealed the most essential groups in the molecule for the antimicrobial activity retention. Active compounds with good MIC range should contain both nonpolar aromatic residues and hydrogen bond donating groups. The best MIC results in selected cases were lower than 1 μg/ml.