Yu. Yu. Morzherin

tert -Amino effect: the Meth-Cohn and Reinhoudt reactions (Review)

The data published over the last 15-20 years on reactions taking place by the tert-amino effect mechanism have been reviewed.

Synthesis of condensed [1,2,3]triazolo-[5,1-b][1,3,4]thiadiazepine systems

In contemporary organic chemistry, rearrangements and transformations of one type of heterocycle to another are promising and convenient methods for the preparation of heterocyclic structures difficult to obtain by other means. However, these reactions are rarely used as a planned method for preparing heterocyclic systems. 1,2,3-Thiadiazoles are convenient starting materials for carrying out various rearrangements. Several rearrangements of 1,2,3-thiadiazoles involving a substituent in the ring position 5 are known [1-3], but only a few of these lead to the preparation of condensed 1,2,3-triazoles. Thus, for example, methods are known for the synthesis of [1,2,3]triazolo[5,1-b][1,3,4]thiadiazines using the Dimroth rearrangement [4, 5].

New Synthetic Cannabinoid – Methyl 2-{[1-(5-Fluoro-Pentyl)-3-Methyl-1H-Indol-3-Ylcarbonyl]-Amino}Butyrate – as a Designer Drug

Synthetic cannabinoids, which are being studied for the purpose of producing new pharmaceutical preparations [1, 2], have changed in recent years into a new form of designer drugs that are being actively circulated illegally throughout the world [3-11]. Whereas until recent times the chemical structures and data from pharmaceutical trials for the distributed compounds had been published in the scientific and patent literature, the distribution of compounds that have not been described in the literature and were synthesized by analogy with narcotic agents that are known and are already prohibited in a number of countries has now become the rule. Here not only compounds of already known groups of synthetic cannabinoids are being synthesized, but new groups are appearing [10, 11]. This fact bears witness to the illegal realization of significant and systematic work on the synthesis of new types of cannabinoids and their testing on the planets population. For this reason, control over the distribution of designer drugs is an important international problem, the first stage in the solution of which is to establish the chemical structure of the newly appearing compounds.

Synthesis of 4-thioacetyl-1,2,3-thiadiazoles. Reversible rearrangement of N-Substituted 5-methyl-1,2,3-thiadiazole-4-carbothioamides

The equilibrium in the reversible rearrangement of 5-methyl-1,2,3-thiadiazole-4-carbothioamides into 5-amino-4-thioacetyl-1,2,3-thiadiazoles is displaced toward the former, and polar solvents favor increased fraction of the thioketone.

Cannabinoids: structures, effects, and classification

The data on the chemical structures, biological effects, and use of cannabinoids on the illegal market of new psychoactive substances were generalized. An extended classification comprising new classes, groups, and subgroups of cannabinoids was proposed for better representation of their structural variety. The emergence of new synthetic cannabinoids which belong to the groups of cycloalkanecarbonylindoles, indole- and indazole-3-carboxamides, and indoleand indazole-3-carboxylates is closely associated with the market of new psychoactive substances.

Criteria for aromaticity of mesoionic heterocycles

The quantum chemical calculations of the basic criteria for aromaticity (nucleus-independent chemical shift (NICS), aromatic stabilization energy (ASE), and parameters of harmonic oscillator model of aromaticity (HOMA), and geometric indices (I5)) of 54 mesoionic heterocycles in the 6–31G* split-valence basis set were performed in terms of the density functional theory (DFT) with the B3LYP exchange-correlation hybrid functional. The aromatic nature of the mesoionic heterocycles containing the pyridinium N atom was shown.

SYNTHESIS AND CYTOTOXIC ACTIVITY OF 1,2,3-TRIAZOLE DERIVATIVES IN GLIOMA CELL CULTURES

A series of 1,2,3-triazole derivatives was prepared and their cytotoxic actions on glioma cell cultures were studied. Amethod for the synthesis of 1-R-5-methyl-1H-[1,2,3]triazole-4-carboxamides is presented, based on transformation of 4-acetyl-1-phenyl-1H-[1,2,3]-triazolate sodium using primary amine hydrochlorides.

Synthesis of fused 3-cyano- and 3-carbamoyl-1,2,3,4-tetrahydroquinolines

A reaction of 3-benzoyl-3-cyano-1,2,3,4-tetrahydroquinolines with hydrazine hydrate is accompanied by elimination of the benzoyl group. A hydration reaction of 3-cyano-1,2,3,4-tetrahydroquinolines leads to 3-carbamoyl-1,2,3,4-tetrahydroquinolines.

1,2,3-Thiadiazolyl Isocyanates in the Synthesis of Biologically Active Compounds. Study of the Cytotoxic Activity of N-(4-methyl-1,2,3-thiadi-azolyl-5-yl)-N'-(4-methylphenyl)Urea*

A simple method is proposed for the synthesis of 1,2,3-thiadiazolylureas by the reaction of 1,2,3-thia-diazolyl isocyanates with primary amines. 1,2,3-Thiadiazolyl isocyanates were obtained in situ by the Curtius rearrangement of 1,2,3-thiadiazolylcarbonyl azides. Cytokinin activity was tested for N-(4-methyl-1,2,3-thiadiazol-5-yl)-N-(4-methylphenyl)urea, which is an analog of thidiazuron, differing in the presence of two methyl groups in the molecule.

Microwave-Assisted Synthesis of Fused 3-Thiocarbamoylquinolines by Reinhoudt Reaction and their Modification by Hantzsch Reaction

We have shown that the reaction of 2-dialkylaminobenzaldehydes with cyanothioacetamide leading to Knoevenagel condensation products and their cyclization according to tert-amino effect mechanism, may be significantly accelerated by using a microwave reactor. The synthesized tetrahydroquinolinо-3-carbothioamides reacted with α-bromoacetophenone in microwave reactor to give 3–(1,3-thiazol-2-yl)tetrahydroquinolines.