5436-38-4

Usage

Class

Methylxanthine

Chemical structure

Purine ring system with three methyl groups and a morpholine ring attached

Natural occurrence

Found in coffee, tea, and other beverages

Uses

Stimulant for the central nervous system, improves mental alertness, increases energy, reduces fatigue

Additional properties

Diuretic, can increase metabolism

Popularity

Ingredient in weight loss supplements, medications, and dietary supplements

Side effects

Insomnia, nervousness, increased heart rate (with excessive consumption)

Upstream product

• 110-91-8 morpholine 
• 4921-49-7 8-chlorocaffeine 
• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 5415-41-8 8-iodo-1,3,7-trimethyl-3,7-dihydro-1 H-purine-2,6-dione 

Relevant academic research and scientific papers

Synthetic Transformations of Sesquiterpene Lactones. 11.* Conjugates Based on Caffeine and Eudesmanolides with N-Containing Linkers

8-(Aminoalkylamino)caffeine or 8-(piperazinyl)caffeine were formed in high yields by reacting 8-bromo- or 8-chlorocaffeine with linear and cyclic diamines using microwave-assisted organic synthesis. These amines were highly reactive in Michael reactions with sesquiterpene lactones containing active methylene groups. Conjugates with caffeine and eudesmanolide moieties bonded by a N-containing linker were synthesized.

Electrochemical C?H Functionalization of (Hetero)Arenes—Optimized by DoE

A novel approach towards the activation of different arenes and purines including caffeine and theophylline is presented. The simple, safe and scalable electrochemical synthesis of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) aryl ethers was conducted using an easy electrolysis setup with boron-doped diamond (BDD) electrodes. Good yields up to 59 percent were achieved. Triethylamine was used as a base as it forms a highly conductive media with HFIP, making additional supporting electrolytes superfluous. The synthesis was optimized using Design of Experiment (DoE) techniques giving a detailed insight to the significance of the reaction parameters. The mechanism was investigated by cyclic voltammetry (CV). Subsequent transition metal-catalyzed as well as metal-free functionalization led to interesting motifs in excellent yields up to 94 percent.

A convenient one-pot synthesis of N-substituted 2-aminoazole derivatives

A practical protocol for the one-pot synthesis of N-substituted 2-aminoazole derivatives is described, employing simple azole substrates, nitrogen nucleophiles, lithium tert-butoxide as the base, and iodine to mediate carbon-nitrogen bond formation. This method proceeds at room temperature under an air atmosphere using a normal benchtop set-up, or can be performed conveniently using microwave irradiation. Georg Thieme Verlag Stuttgart - New York.