Ivan V. Dyachenko

The review systemizes literature data over the past 10–15 years on the synthesis of 2-chalcogen-substituted nicotinonitriles and their derivatives from cyano(seleno,thio)acetamides and other reagents. In addition, some information on biologically active compounds of this series is given. The bibliography includes 280 references.

A three-component reaction of carbocyclic enaminoketones, CH-acids, and electrophiles was studied. Based on the reaction of nucleophilic vinyl substitution (SVin), previously unknown derivatives of 5,6,7,8-tetrahydroisoquinolines were synthesized. The structure of a number of products was studied by X-ray diffraction.

The three-component reaction of carbocyclic enamino ketones, CH acids, and electrophiles has been studied. Previously unknown 5,6,7,8-tetrahydroisoquinoline derivatives have been synthesized via nucleophilic vinylic substitution (S_NVin). The structures of some of the obtained compounds have been determined by X-ray analysis.

The chemistry of heterocyclic compounds has traditionally been and remains a bright area of chemical science in Russia. This is due to the fact that many heterocycles find the widest application. These compounds are the key structural fragments of most drugs, plant protection agents. Many natural compounds are also derivatives of heterocycles. At present, more than half of the hundreds of millions of known chemical compounds are heterocycles. This collective review is devoted to the achievements of Russian chemists in this field over the last 15–20 years. The review presents the achievements of leading heterocyclists representing both RAS institutes and university science. It is worth noting the wide scope of the review, both in terms of the geography of author teams, covering the whole of our large country, and in terms of the diversity of research areas. Practically all major types of heterocycles are represented in the review. The special attention is focused on the practical applications of heterocycles in the design of new drugs and biologically active compounds, high-energy molecules, materials for organic electronics and photovoltaics, new ligands for coordination chemistry, and many other rapidly developing areas. These practical advances would not be possible without the development of new fundamental transformations in heterocyclic chemistry. Bibliography — 2237 references.

Multicomponent condensation of cyanothioacetamide, carbonyl compounds, enamines and alkylating reagents initiated by the Knoevenagel reaction led to the formation of 2-thionicotinonitriles. The molecular and crystal structure of the prepared products was studied by single crystal X-ray diffraction method.

New nicotinamide derivatives have been synthesized by reactions of enamino ketones, aryl(hetaryl)­methylidenecyanothioacetamides, alkylating agents, formamide, and cycloalkanones. The structure of some of the synthesized compounds has been determined by X-ray analysis.

Multicomponent condensation of alkylating reagents with carbonyl compounds functionalized by CH-acids is initiated by the Knoevenagel reaction and leads to the formation of substituted pyridines, thienopyridines, pyridothienopyridines, and pyrimidothienopyridopyrimidines. The structure of the key products was studied by the X-ray diffraction method.

New cycloalka[b]pyridine and chromene derivatives were synthesized by multicomponent con­densa­tions. The structure of some of the synthesized compounds was determined by X-ray analysis.