|Molar mass||70.10 g·mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|(: / ?)|
2-Imidazoline (dihydroimidazoles) is one of three isomers of the
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Imidazoles can be prepared from dehydrogenation of imidazolines.
Imidazolines as Precursors of Imidazoles
Imidazoline derivatives have extensive applications in surfactant in small proportions for improving detergent qualities for various purposes (fabric softeners, hair and fabric conditioning).
As a structural analogue of 2-oxazolines, 2-imidazolines have been developed as ligands in coordination chemistry. The substitutions on the nitrogen atom in the imidazoline ring provide opportunities for fine-tuning the electronic and steric properties. Some of the complexes function as catalysts for Suzuki–Miyaura couplings, Mizoroki–Heck reactions, Diels–Alder reactions, asymmetric allylic substitution, [3,3] sigmatropic rearrangement, Henry reactions, etc.
Second generation Grubbs' catalyst
2-imidazolines have been investigated as antihyperglycemic, anti-inflammatory, antihypertensive, antihypercholesterolemic, and antidepressant reagents.The imidazoline-containing drug clonidine is used alone or in combination with other medications to treat high blood pressure. It is also used in the treatment of dysmenorrhea, hypertensive crisis, Tourette's syndrome and attention deficit hyperactivity disorder (ADHD).
Imidazoline has been found in various natural products. Natural molecules topsentin D and spongotine B were discovered in several marine sponges. These metabolites have received considerable attention because of their potent properties such as antitumor, antiviral, and anti-inflammatory activities.
Imidazoline in Natural Products
A variety of routes exist for the synthesis of imidazolines, with the most common methods involving the condensation of 1,2-diamines with nitriles or esters. The nitrile based route is effective for both alkyl and aryl nitriles and requires high temperatures or acid catalysis.
Synthesis of Imidazoline
Many imidazolines are biologically active. Most bio-active derivatives bear a substituent (aryl or alkyl group) on the carbon between the nitrogen centers. Some generic names include oxymetazoline, xylometazoline, tetrahydrozoline, and naphazoline.
- Biological role 1
- Synthesis of Imidazoline 2
- Imidazoline in Natural Products 3
- Pharmaceutical Applications 4
- Homogeneous Catalysis 5
- Industrial Applications 6
- Imidazolines as Precursors of Imidazoles 7
- See also 8
- References 9