Pyrimidines are aromatic compounds composed of carbon and nitrogen atoms in a six-membered ring. Pyrimidines generally refer to pyrimidine and its derivatives. Pyrimidine (C4H4N2) is one of the simplest pyrimidines which has aromatic ring composed of two nitrogen atoms and four carbon atoms, with hydrogen atoms attached to each carbon. Pyrimidine has a melting point of 22.5 °C and a boiling point of 123-124 °C. It is soluble in water and ethanol, and is weakly alkaline in water.
The carbon and nitrogen atoms of pyrimidine are connected via alternating double and single bonds. This bond structure allows for resonance, or aromaticity, causing the ring to be very stable. On the other hand, the conjugated π bonds in planar pyrimidines can also form a TATB-like network crystal structure. High-density crystals are obtained by π-π stacking between layers, and their planar conformation is also conducive to the formation of hydrogen bonds, resulting in better thermal stability. For pyrimidine, there is no direct use, but pyrimidine derivatives exist widely in nature. The pyrimidine derivatives such as cytosine, uracil, thymine are important components of nucleic acid. As an important class of organic chemicals, pyrimidine and its derivatives have many applications in organic synthesis, as follows:
Pyrimidine derivatives have become one of the hotspots in the field of modern pesticide synthesis due to their biological activities such as insecticidal, bactericidal, herbicidal and plant growth regulation, and unique mechanisms of action. Pyrimidine can be used in the synthesis of diazinon, pyrimidinol, blasticidin, herbicide, pyridoxine, pyridoxine, cyclophanate, promethazine, ethabendil, sulfamethoxazole, pyrazinone, pirimicarb, ethyl fenfen, fenfen, polyoxomycin, pyrimidine, pyrimidinphos, oxazophos, azoxymethylene alcohol, isopyrimoxol and other pesticides.
The pyrimidine group is a diazine structure, and the positive charge of the carbon atom on the nucleus is weak, so the pyrimidine reactive dye is the most difficult to hydrolyze, and the dye-fiber bond has high stability, especially suitable for high temperature dyeing. Pyrimidine and its derivatives can be used to synthesize dyes, such as dyes with trihalogenated pyrimidine cores, which react well with fibers.
Pyrimidine and its derivatives can be used to synthesize a variety of drugs, such as vitamin B, sulfadiazine, sulfamethazine, and sulfadimethoxine. Furthermore, 5-FU is one of the most famous pyrimidine derivatives used as antineoplastic agent. 5-FU has broad-spectrum antimicrobial activity and inhibits virulence factor and biofilm production.
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