Nitro-functionalized analogues of 1,3-Butadiene: An overview of characteristic, synthesis, chemical transformations and biological activity

Abstract

The nitrovinyl moiety is surely one of the most reactive fragments in organic chemistry, continuously employed to explore original pathways and reach new targets. One of the most important classes of chemicals containing this fragment are nitro-functionalised analogues of 1,3-butadiene. In this paper a comprehensive review study of these compounds is performed. The manuscript includes an analysis of physicochemical properties, spectral characteristic, synthesis, biological activity, and possible transformations of nitro substituted analogues of 1,3-butadiene. The analysis was divided into several parts, depending on the number of nitro groups included in the structure of a 1,3-butadiene analogue. In addition, the work includes information about hazards and safety principles when working with nitro compounds. Based on the analysis of the literature, it can be concluded that nitro-functionalised analogues of 1,3-butadiene exhibit diversified profile of properties, and an outstanding potential as valuable reagents in organic synthesis useful to obtain heterocycles that can be applied in medicine.

Synthesis of β-amino alcohols by ring opening of epoxides with amines catalyzed by sulfated tin oxide under mild and solvent-free conditions

“…IR spectra were recorded on a Perkin Elmer FTIR-240 C spectrophotometer. 1 H and 13 C NMR spectra were recorded on Bruker Avance 300 MHz spectrophotometer. Chemical shifts are given in ppm with respect to internal TMS and J values are quoted in Hz.…”

“…They serve as the foundation for, or are components of, a wide range of industrial goods, such as lubricants, solvents, polymers, fuels, and explosives, as well as pharmaceuticals, petrochemicals, and agrichemicals. [1][2][3][4][5][6][7][8][9][10][11] In synthetic chemistry, the ability to open the rings of epoxides and introduce amino functionality into oxiranes to produce β-amino alcohols is becoming increasingly important. β-amino alcohols are a significant class of chemical molecules with several applications, including the production of unnatural amino acids, 12 chiral auxillaries for asymmetric synthesis, 13 and a wide range of physiologically active natural and synthesized products.…”

(1E,3E)-1,4-Dinitro-1,3-butadiene—Synthesis, Spectral Characteristics and Computational Study Based on MEDT, ADME and PASS Simulation

“…In recent times, another class of nitro-unsaturated organic compounds—conjugated nitro dienes (CNDs)—are increasing in popularity [ 22 , 23 ]. Due to their structure, these compounds offer many more possibilities for transformation compared to CNAs [ 24 ].…”

“…However, the number of examples of the use of CNDs in CA reactions as well as in 6π-e − processes is strongly limited. Reactions described in the literature that tackle the application of these compounds in organic synthesis are predominantly limited to nucleophilic additions and substitutions with thiols and amines; there are fewer examples of electrophilic additions of halogens [ 22 , 23 , 24 , 25 ]. Therefore, the use of CNDs as building blocks to obtain heterocyclic systems is an attractive course of research and determines one of the most promising trends in current organic synthesis.…”

“…Despite the fact that the chemistry of CNDs has been known since the middle of the twentieth century, there are still many gaps in the synthesis and spectral characteristics of these compounds [ 23 ]. What is more, numerous protocols and reports presented in the scientific literature are incomplete.…”