Current Organic Synthesis - Volume 19, Issue 3, 2022

Selenium promoted-cyclization of unsaturated substrates containing internal nitrogen nucleophiles, such as different amines and amides, including the examples of its application in the synthesis of more complex polycyclic compounds is reviewed. Selenocyclization reactions of some more specific polyfunctional substrates, like Biginelli hybrids and hydantoins, are also covered.

Organoselenium chemistry has undergone extensive development during the past decades, mostly due to the unique chemical properties of organoselenium compounds that have been widely explored in a number of synthetic transformations, as well as due to the interesting biological properties of these compounds. Diselenides and selenocyanates constitute the promising classes of organoselenium compounds that possess interesting biological effects, and that can be used in the preparation of other selenium compounds. The combination of diselenide and selenocyanate moieties with other biologically relevant molecules (such as heterocycles, steroids, etc.) is a way for the development of compounds with promising pharmaceutical potential. Therefore, the aim of this review is to highlight the recent achievements in the use of diselenides or selenocyanates as precursors for the synthesis of pharmaceutically relevant compounds, preferentially compounds with antitumor and antimicrobial activities.

For many years since its discovery, Selenium has played the role of a bad boy who became a hero in organic transformations. Selenium dioxide, for instance, is one of the most remembered reagents in allylic oxidations, having been applied in the synthesis of several naturally occurring products. The main goal of this review is to show the recent advances in the use of classical and new selenium reagents in organic synthesis. As demonstrated through the around 60 references discussed here, selenium can go even forward as a versatile reagent. We bring a collection of selenium reagents and their transformations that still asleep in the eyes of most synthetic organic chemists.

Organoselenium chemistry has emerged as a distinctive area of research with tremendous utility in the synthesis of biologically and pharmaceutically active molecules. Significant synthetic approaches have been made for the construction of C-Se bonds, which are useful in other organic transformations. This review focuses on the versatility of transition metal-mediated selenylation reactions, providing insights into various synthetic pathways and mechanistic details. Furthermore, this review aims to offer a broad perspective for designing efficient and novel catalysts to incorporate organoselenium moiety into the inert C-H bonds.

Organoselenium chemistry has developed as an important tool in the field of synthetic and medicinal chemistry. Various organoselenium reagents have been developed and used successfully to achieve different organic transformations such as selenocyclizations, oxyselenenylations, selenoxide eliminations, etc. Additionally, organoselenium reagents' potential is not limited to their use as stoichiometric reagents, but they have been successfully used as organocatalysts in a number of synthetic transformations. Various organic and inorganic oxidants have been identified as terminal oxidants to regenerate the active catalytic species. In this review article, the recent progress of organoselenium reagents in catalysis is being highlighted along with their asymmetric variants.

The natural terpene limonene is widely found in nature. The (R)-limonene (the most abundant enantiomer) is present in the essential oils of lemon, orange, and other citrus fruits, while the (S)- limonene is found in peppermint and the racemate in turpentine oil. Limonene is a low-cost, low toxicity biodegradable terpene present in agricultural wastes derived from citrus peels. The products obtained from the conversion of limonene are valuable compounds widely used as additives for food, cosmetics, or pharmaceuticals. The conversion of limonene to produce different products has been the subject of intense research, mainly with the objective of improving catalytic systems. This review focused on the application of heterogeneous catalysts in the catalytic conversion of limonene.

Recent advances in the environmentally benign synthesis of common heterocycles are described. This account features three main parts; the preparation of non-aromatic heterocycles, one-ring aromatic heterocycles and their condensed analogs. Due to the great variety of and high interest in these compounds, this work focuses on providing representative examples of the preparation of the target compounds.

Aims: In this paper, we report on the synthesis and liquid crystalline properties of some low molecular weight bis-chalcone compounds derived from acetone, cyclopentanone and cyclohexanone mesogenic cores. Background: Structurally bis-chalcones belong to a broader family of chalcone compounds. Chalcone is a compound that consists of two aromatic rings linked by an unsaturated α, β-ketone. Objective: Liquid crystalline chalcones are prepared by aliphatic chain substituents on two aromatic rings. Chalcones are well studied for their mesomorphic properties. Compared to a large number of chalcone based LCs reported, only a few articles have been published on the mesomorphic properties of bis-chalcone compounds. The target compounds of the present study varied not only in their central core but also in number and position of terminal aliphatic chain substitution-a key structural unit in deciding the liquid crystalline properties of a compound. Methods: All target compounds were synthesized in good yield by base catalyzed Claisen-Schmidt condensation reaction. Molecular structures were confirmed by FT-IR, ¹H NMR, ¹³C NMR, and mass spectroscopic methods. Liquid crystalline property of these compounds was evaluated using polarizing optical microscopy and differential scanning calorimetry. Results: Although none of the acetone based compounds exhibited mesomorphism, cyclopentanone and cyclohexanone based compounds with octyloxy chain at para position on either side of the dibenzylidine ring stabilized liquid crystalline smectic (SmA and SmC) and nematic (N) phases. The observed structure-liquid crystalline property relationship was explained by structural analysis of molecules using DFT calculations. Considering the inherent photoluminescence nature of the chalcone moiety, a preliminary study was carried out on a selected compound to reveal its fluorescence property. Conclusion: Our study brings about an important structure-liquid crystalline property relationship in a relatively unexplored class of bis-chalcone liquid crystals.