Ivanova Elizaveta, Osipova Margarita, Kadyrov Yhtyyar, Karpov Sergey, Markova Svetlana, Zazhivihina Ekaterina, Umanova Lubov, Vasilieva Tatyana, Mitrasov Yurii, Smolkina Yulia, Nasakin Oleg
Organic and Pharmaceutical Chemistry Department, Ulyanov Chuvash State University, Moskovsky Prospect, 15, 428015 Cheboksary, Russia.
Department of Scientific Chemistry Education, Yakovlev Chuvash State Pedagogical University, K. Marx Street, 38, 428000 Cheboksary, Russia.
Molecules. 2024 Oct 6;29(19):4727. doi: 10.3390/molecules29194727.
The significant synthetic potential and reactivity of tetracyanoethylene (TCNE) have captured the interest of numerous chemical communities. One of the most promising, readily achievable, yet least explored pathways for the reactivity of TCNE involves its interaction with arylamines. Typically, the reaction proceeds via tricyanovinylation (TCV); however, deviations from the standard chemical process have been observed in some instances. These include the formation of heterocyclic structures through tricyanovinyl intermediates, aliphatic dicarbonitriles through the cleavage of the C-C bond of a tetracyanoethyl substituent, complexation, and various pericyclic reactions. Therefore, the objective of this study is to review the diverse modes of interaction of TCNE with aromatic nitrogen-containing compounds and to focus the attention of the chemical community on the synthetic capabilities of this reagent, as well as the various biological and optical activities of the structures synthesized based on TCNE.
四氰基乙烯（TCNE）巨大的合成潜力和反应活性引起了众多化学领域的关注。对于TCNE的反应活性而言，最具前景、最容易实现但探索最少的途径之一涉及它与芳胺的相互作用。通常，该反应通过三氰基乙烯基化（TCV）进行；然而，在某些情况下已观察到偏离标准化学过程的情况。这些情况包括通过三氰基乙烯基中间体形成杂环结构、通过四氰基乙基取代基的C-C键断裂形成脂肪族二腈、络合以及各种周环反应。因此，本研究的目的是综述TCNE与含芳族氮化合物相互作用的多种模式，并使化学界关注该试剂的合成能力，以及基于TCNE合成的结构的各种生物和光学活性。
